Stereoelectronic Control in the Ozone‐Free Synthesis of Ozonides

The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone‐free synthesis of bridged secondary ozonides from 1,5‐dicarbonyl compounds and H2O2. The tetraoxane products generally formed in reactions of carbonyl and dicarbonyl compounds with H2O2 were not detected...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 56; no. 18; pp. 4955 - 4959
Main Authors dos Passos Gomes, Gabriel, Yaremenko, Ivan A., Radulov, Peter S., Novikov, Roman A., Chernyshev, Vladimir V., Korlyukov, Alexander A., Nikishin, Gennady I., Alabugin, Igor V., Terent'ev, Alexander O.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 24.04.2017
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
anomeric effect
Carbon
Carbonyl compounds
Carbonyls
Chemistry
Chemistry, Multidisciplinary
Deactivation
Distortion
Guidelines
Hydrogen peroxide
Ozone
Ozonides
peroxides
Physical Sciences
Science & Technology
stereoelectronic control
synthetic methods
GEM-DIHYDROPEROXIDES
GEMINAL BISHYDROPEROXIDES
IODINE
peroxides
stereoelectronic control
DISPIRO-1,2,4,5-TETRAOXANES
ozonides
MILD
KETONES
BRIDGED 1,2,4,5-TETRAOXANES
anomeric effect
HYDROGEN-PEROXIDE
CYCLIC PEROXIDES
ARTEMISININ
synthetic methods
Online AccessGet full text

Cover

Abstract The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone‐free synthesis of bridged secondary ozonides from 1,5‐dicarbonyl compounds and H2O2. The tetraoxane products generally formed in reactions of carbonyl and dicarbonyl compounds with H2O2 were not detected because the structural distortions imposed on the tetraoxacyclohexane subunit in [3.2.2]tetraoxanonanes by the three‐carbon bridge leads to the partial deactivation of anomeric effects. The new procedure is readily scalable to produce gram quantities of the ozonides. This reaction enables the selective preparation of ozonides without the use of ozone. Ozonides without the ozone: The synthesis of bridged secondary ozonides from 1,5‐dicarbonyl compounds and H2O2 was guided by stereoelectronic considerations (see scheme). The tetraoxane products usually formed under these conditions were not detected owing to the partial deactivation of anomeric effects as a result of distortion of the tetraoxacyclohexane subunit in the [3.2.2]tetraoxanonane intermediates by the three‐carbon bridge.
AbstractList The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone-free synthesis of bridged secondary ozonides from 1,5-dicarbonyl compounds and H2 O2 . The tetraoxane products generally formed in reactions of carbonyl and dicarbonyl compounds with H2 O2 were not detected because the structural distortions imposed on the tetraoxacyclohexane subunit in [3.2.2]tetraoxanonanes by the three-carbon bridge leads to the partial deactivation of anomeric effects. The new procedure is readily scalable to produce gram quantities of the ozonides. This reaction enables the selective preparation of ozonides without the use of ozone.The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone-free synthesis of bridged secondary ozonides from 1,5-dicarbonyl compounds and H2 O2 . The tetraoxane products generally formed in reactions of carbonyl and dicarbonyl compounds with H2 O2 were not detected because the structural distortions imposed on the tetraoxacyclohexane subunit in [3.2.2]tetraoxanonanes by the three-carbon bridge leads to the partial deactivation of anomeric effects. The new procedure is readily scalable to produce gram quantities of the ozonides. This reaction enables the selective preparation of ozonides without the use of ozone.
The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone‐free synthesis of bridged secondary ozonides from 1,5‐dicarbonyl compounds and H 2 O 2 . The tetraoxane products generally formed in reactions of carbonyl and dicarbonyl compounds with H 2 O 2 were not detected because the structural distortions imposed on the tetraoxacyclohexane subunit in [3.2.2]tetraoxanonanes by the three‐carbon bridge leads to the partial deactivation of anomeric effects. The new procedure is readily scalable to produce gram quantities of the ozonides. This reaction enables the selective preparation of ozonides without the use of ozone.
The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone-free synthesis of bridged secondary ozonides from 1,5-dicarbonyl compounds and H O . The tetraoxane products generally formed in reactions of carbonyl and dicarbonyl compounds with H O were not detected because the structural distortions imposed on the tetraoxacyclohexane subunit in [3.2.2]tetraoxanonanes by the three-carbon bridge leads to the partial deactivation of anomeric effects. The new procedure is readily scalable to produce gram quantities of the ozonides. This reaction enables the selective preparation of ozonides without the use of ozone.
The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone-free synthesis of bridged secondary ozonides from 1,5-dicarbonyl compounds and H2O2. The tetraoxane products generally formed in reactions of carbonyl and dicarbonyl compounds with H2O2 were not detected because the structural distortions imposed on the tetraoxacyclohexane subunit in [3.2.2]tetraoxanonanes by the three-carbon bridge leads to the partial deactivation of anomeric effects. The new procedure is readily scalable to produce gram quantities of the ozonides. This reaction enables the selective preparation of ozonides without the use of ozone.
The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone‐free synthesis of bridged secondary ozonides from 1,5‐dicarbonyl compounds and H2O2. The tetraoxane products generally formed in reactions of carbonyl and dicarbonyl compounds with H2O2 were not detected because the structural distortions imposed on the tetraoxacyclohexane subunit in [3.2.2]tetraoxanonanes by the three‐carbon bridge leads to the partial deactivation of anomeric effects. The new procedure is readily scalable to produce gram quantities of the ozonides. This reaction enables the selective preparation of ozonides without the use of ozone. Ozonides without the ozone: The synthesis of bridged secondary ozonides from 1,5‐dicarbonyl compounds and H2O2 was guided by stereoelectronic considerations (see scheme). The tetraoxane products usually formed under these conditions were not detected owing to the partial deactivation of anomeric effects as a result of distortion of the tetraoxacyclohexane subunit in the [3.2.2]tetraoxanonane intermediates by the three‐carbon bridge.
Author Alabugin, Igor V.
Terent'ev, Alexander O.
Yaremenko, Ivan A.
dos Passos Gomes, Gabriel
Radulov, Peter S.
Novikov, Roman A.
Korlyukov, Alexander A.
Nikishin, Gennady I.
Chernyshev, Vladimir V.
Author_xml – sequence: 1
  givenname: Gabriel
  orcidid: 0000-0002-8235-5969
  surname: dos Passos Gomes
  fullname: dos Passos Gomes, Gabriel
  organization: Florida State University
– sequence: 2
  givenname: Ivan A.
  orcidid: 0000-0003-1068-9051
  surname: Yaremenko
  fullname: Yaremenko, Ivan A.
  organization: All-Russian Research Institute for Phytopathology
– sequence: 3
  givenname: Peter S.
  surname: Radulov
  fullname: Radulov, Peter S.
  organization: All-Russian Research Institute for Phytopathology
– sequence: 4
  givenname: Roman A.
  surname: Novikov
  fullname: Novikov, Roman A.
  organization: Russian Academy of Sciences
– sequence: 5
  givenname: Vladimir V.
  surname: Chernyshev
  fullname: Chernyshev, Vladimir V.
  organization: A. N. Frumkin Institute of Physical Chemistry and Electrochemistry
– sequence: 6
  givenname: Alexander A.
  surname: Korlyukov
  fullname: Korlyukov, Alexander A.
  organization: Russian Academy of Sciences
– sequence: 7
  givenname: Gennady I.
  surname: Nikishin
  fullname: Nikishin, Gennady I.
  organization: Russian Academy of Sciences
– sequence: 8
  givenname: Igor V.
  orcidid: 0000-0001-9289-3819
  surname: Alabugin
  fullname: Alabugin, Igor V.
  email: alabugin@chem.fsu.edu
  organization: Florida State University
– sequence: 9
  givenname: Alexander O.
  orcidid: 0000-0001-8018-031X
  surname: Terent'ev
  fullname: Terent'ev, Alexander O.
  email: terentev@ioc.ac.ru
  organization: All-Russian Research Institute for Phytopathology
BackLink https://www.ncbi.nlm.nih.gov/pubmed/28378382$$D View this record in MEDLINE/PubMed
BookMark eNqNkkuLFDEQgIOsuA-9epQGL4L0mEcnqRzXZlcXFvewem4y6WrM0pOsSTcynvwJ_sb9JZtxxhEWfOSSIvm-qqKoY3IQYkBCnjO6YJTyNzZ4XHDKFKPKmEfkiEnOaqG1OChxI0StQbJDcpzzTeEBqHpCDjkIDQL4EXl7PWHCiCO6KcXgXdXGUKKx8qGaPmN19a0UvPv-4zwhVtfrUN6yz1Ucfv74HvNT8niwY8Znu_uEfDo_-9i-ry-v3l20p5e1awSYWva9UspqVMYJWA6WM6obCtb2YtP9YBx3qBwTRsueoQHOQIpewtKpnitxQl5t896m-GXGPHUrnx2Oow0Y59wxgKbRXFJZ0JcP0Js4p1C665ihUpeCZTZ_o6AcaYSmhXqxo-blCvvuNvmVTevu1wwL8HoLfMVlHLLzGBzuMUqpMEZAo0tEodDw_3TrJzv5GNo4h6moi63qUsw54bDXGO0229BttqHbb0MRmgeC2yWckvXjnzWza9GPuP5Hke70w8XZb_ced6jFUw
CODEN ACIEAY
CitedBy_id crossref_primary_10_1002_anie_201903690
crossref_primary_10_1039_D1CS00386K
crossref_primary_10_1039_C9SC06511C
crossref_primary_10_1002_anie_202014974
crossref_primary_10_1021_jacs_0c06294
crossref_primary_10_1002_anie_201712651
crossref_primary_10_1016_j_tet_2018_09_023
crossref_primary_10_1021_acs_orglett_2c02551
crossref_primary_10_1021_jacs_4c14062
crossref_primary_10_1002_adsc_202300881
crossref_primary_10_59761_RCR5125
crossref_primary_10_1007_s11172_024_4366_8
crossref_primary_10_1021_jacs_1c02249
crossref_primary_10_1002_wcms_1389
crossref_primary_10_1016_j_tet_2025_134492
crossref_primary_10_1002_chem_201701755
crossref_primary_10_1002_ange_201712651
crossref_primary_10_3390_molecules28134913
crossref_primary_10_1016_j_jphotochem_2020_112553
crossref_primary_10_1002_chem_201904555
crossref_primary_10_3390_chemistry6050072
crossref_primary_10_1021_jacs_7b05367
crossref_primary_10_1002_ange_202014974
crossref_primary_10_1002_ange_201807247
crossref_primary_10_1021_acs_joc_8b00130
crossref_primary_10_1134_S0036024420040238
crossref_primary_10_1002_ange_201903690
crossref_primary_10_1002_ange_201807485
crossref_primary_10_3390_ph15040472
crossref_primary_10_1002_cmdc_201700804
crossref_primary_10_1021_acs_jnatprod_9b00393
crossref_primary_10_2174_1568026619666190620143848
crossref_primary_10_1021_acs_jpca_8b05212
crossref_primary_10_1021_acs_joc_4c00233
crossref_primary_10_1021_acs_orglett_9b00425
crossref_primary_10_1021_jacs_2c00406
crossref_primary_10_1039_C9CP05744G
crossref_primary_10_1002_anie_201807485
crossref_primary_10_1039_C9NJ01446B
crossref_primary_10_1002_cmdc_202000042
crossref_primary_10_1002_anie_201807247
crossref_primary_10_1134_S1070428019010123
crossref_primary_10_1002_chem_201903752
crossref_primary_10_1021_acs_joc_8b02218
crossref_primary_10_1021_acs_joc_8b02779
crossref_primary_10_1039_D2CC05029C
crossref_primary_10_1039_D0SC01025A
Cites_doi 10.1039/c3ra42513d
10.1002/cber.19530860102
10.1055/s-0034-1378210
10.1002/jlac.199719970715
10.1021/jo0708745
10.1039/c3ob27239g
10.1134/S1070428015120027
10.1021/jm00094a015
10.1039/a705725c
10.1016/j.tet.2005.11.022
10.1135/cccc19720263
10.1002/hlca.19770600618
10.1016/j.tetlet.2007.07.012
10.1021/jo202437r
10.3390/molecules15031433
10.1016/j.tetlet.2008.11.055
10.1021/ol8023874
10.1021/ol500835f
10.1002/jlac.19535830102
10.1016/j.bmcl.2008.01.053
10.1002/cber.19640971116
10.1039/b917056a
10.1021/jo4001564
10.1002/chem.201402594
10.1021/acs.orglett.5b02296
10.1039/C5SC02402A
10.1021/ol900262t
10.1016/j.bmcl.2008.10.083
10.1039/c4gc00586d
10.1002/9781118906378
10.1016/S0065-2490(97)80016-0
10.1021/jo071072c
10.1002/cber.19550881210
10.1021/jm990014j
10.1080/00397910701226384
10.1021/jo502344x
10.1007/s11172-013-0316-6
10.1021/acs.orglett.5b01307
10.1080/00397911.2011.610549
10.1039/b809661a
10.1021/ol060590r
10.1021/jm990530
10.1021/jm030571c
10.1016/S0020-7519(02)00195-9
10.1021/jo7027213
10.3762/bjoc.10.6
10.1021/ol801859c
10.1021/jo00096a059
10.1016/j.cbpa.2007.05.038
10.1055/s-0029-1217394
10.1002/(SICI)1099-0690(199804)1998:4<627::AID-EJOC627>3.0.CO;2-N
10.1021/jo900226b
10.1039/b503402g
10.1039/C4CC05098C
10.1002/ejoc.201500919
10.1135/cccc20051447
10.1002/adsc.201100561
10.1002/cber.19751080533
10.1039/c4cc05098c
10.1039/c5sc02402a
ContentType Journal Article
Copyright 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Copyright_xml – notice: 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
– notice: 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
– notice: 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
DBID AAYXX
CITATION
17B
1KM
1KN
BLEPL
DTL
EGQ
GYRTJ
NPM
7TM
K9.
7X8
DOI 10.1002/anie.201610699
DatabaseName CrossRef
Web of Knowledge
Index Chemicus
Current Chemical Reactions
Web of Science Core Collection
Science Citation Index Expanded
Web of Science Primary (SCIE, SSCI & AHCI)
Web of Science - Science Citation Index Expanded - 2017
PubMed
Nucleic Acids Abstracts
ProQuest Health & Medical Complete (Alumni)
MEDLINE - Academic
DatabaseTitle CrossRef
Web of Science
PubMed
ProQuest Health & Medical Complete (Alumni)
Nucleic Acids Abstracts
MEDLINE - Academic
DatabaseTitleList MEDLINE - Academic
CrossRef
PubMed
ProQuest Health & Medical Complete (Alumni)

ProQuest Health & Medical Complete (Alumni)
Web of Science
Database_xml – sequence: 1
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
– sequence: 2
  dbid: 1KN
  name: Current Chemical Reactions
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1521-3773
Edition International ed. in English
EndPage 4959
ExternalDocumentID 4321765307
28378382
000399384700008
10_1002_anie_201610699
ANIE201610699
Genre shortCommunication
Research Support, Non-U.S. Gov't
Journal Article
GrantInformation_xml – fundername: Russian Foundation for Basic Research
  funderid: Grant 15-29-05820; 14-03-00237
– fundername: Division of Chemistry
  funderid: CHE-1465142
– fundername: Russian Foundation for Basic Research; Russian Foundation for Basic Research (RFBR); Spanish Government
  grantid: 14-03-00237; 15-29-05820 ofi_m
– fundername: National Science Foundation; National Science Foundation (NSF)
  grantid: CHE-1465142
– fundername: IBM; International Business Machines (IBM)
GroupedDBID ---
-DZ
-~X
.3N
.GA
05W
0R~
10A
1L6
1OB
1OC
1ZS
23M
33P
3SF
3WU
4.4
4ZD
50Y
50Z
51W
51X
52M
52N
52O
52P
52S
52T
52U
52W
52X
53G
5GY
5RE
5VS
66C
6TJ
702
7PT
8-0
8-1
8-3
8-4
8-5
8UM
930
A03
AAESR
AAEVG
AAHQN
AAMNL
AANLZ
AAONW
AASGY
AAXRX
AAYCA
AAZKR
ABCQN
ABCUV
ABDBF
ABEML
ABIJN
ABJNI
ABLJU
ABPPZ
ABPVW
ACAHQ
ACCZN
ACFBH
ACGFS
ACIWK
ACNCT
ACPOU
ACPRK
ACSCC
ACXBN
ACXQS
ADBBV
ADEOM
ADIZJ
ADKYN
ADMGS
ADOZA
ADXAS
ADZMN
AEIGN
AEIMD
AETEA
AEUYR
AEYWJ
AFBPY
AFFNX
AFFPM
AFGKR
AFRAH
AFWVQ
AFZJQ
AGHNM
AGYGG
AHBTC
AHMBA
AITYG
AIURR
AJXKR
ALAGY
ALMA_UNASSIGNED_HOLDINGS
ALUQN
ALVPJ
AMBMR
AMYDB
ATUGU
AUFTA
AZBYB
AZVAB
BAFTC
BDRZF
BFHJK
BHBCM
BMNLL
BMXJE
BNHUX
BROTX
BRXPI
BTSUX
BY8
CS3
D-E
D-F
D0L
DCZOG
DPXWK
DR1
DR2
DRFUL
DRSTM
EBS
EJD
F00
F01
F04
F5P
G-S
G.N
GNP
GODZA
H.T
H.X
HBH
HGLYW
HHY
HHZ
HZ~
IX1
J0M
JPC
KQQ
LATKE
LAW
LC2
LC3
LEEKS
LH4
LITHE
LOXES
LP6
LP7
LUTES
LW6
LYRES
M53
MEWTI
MK4
MRFUL
MRSTM
MSFUL
MSSTM
MXFUL
MXSTM
N04
N05
N9A
NF~
NNB
O66
O9-
OIG
P2P
P2W
P2X
P4D
PQQKQ
Q.N
Q11
QB0
QRW
R.K
RNS
ROL
RX1
RYL
SUPJJ
TN5
UB1
UPT
V2E
W8V
W99
WBFHL
WBKPD
WH7
WIB
WIH
WIK
WJL
WOHZO
WQJ
WXSBR
WYISQ
XG1
XPP
XSW
XV2
YZZ
ZZTAW
~IA
~KM
~WT
AAHHS
AAYXX
ACCFJ
ADZOD
AEEZP
AEQDE
AIWBW
AJBDE
CITATION
17B
1KM
1KN
BLEPL
DTL
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
GROUPED_WOS_WEB_OF_SCIENCE
NPM
7TM
K9.
7X8
ID FETCH-LOGICAL-c4389-5dd666a7e69c38bfa2107408aad36106f9c2ce6c13975d1e9821853d58bc6d263
IEDL.DBID DR2
ISICitedReferencesCount 42
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000399384700008
ISSN 1433-7851
1521-3773
IngestDate Thu Jul 10 18:44:31 EDT 2025
Sun Jul 13 05:35:23 EDT 2025
Sun Jul 13 04:16:22 EDT 2025
Mon Jul 21 05:38:35 EDT 2025
Fri Aug 29 16:11:57 EDT 2025
Tue Jul 29 09:14:17 EDT 2025
Tue Jul 01 03:27:29 EDT 2025
Thu Apr 24 23:02:03 EDT 2025
Wed Aug 20 07:26:12 EDT 2025
IsPeerReviewed true
IsScholarly true
Issue 18
Keywords GEM-DIHYDROPEROXIDES
GEMINAL BISHYDROPEROXIDES
IODINE
peroxides
stereoelectronic control
DISPIRO-1,2,4,5-TETRAOXANES
ozonides
MILD
KETONES
BRIDGED 1,2,4,5-TETRAOXANES
anomeric effect
HYDROGEN-PEROXIDE
CYCLIC PEROXIDES
ARTEMISININ
synthetic methods
Language English
License http://onlinelibrary.wiley.com/termsAndConditions#am
http://onlinelibrary.wiley.com/termsAndConditions#vor
2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
LinkModel DirectLink
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-c4389-5dd666a7e69c38bfa2107408aad36106f9c2ce6c13975d1e9821853d58bc6d263
Notes These authors contributed equally.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
content type line 23
ORCID 0000-0003-1068-9051
0000-0001-9289-3819
0000-0001-8018-031X
0000-0002-8235-5969
0000-0001-6056-3065
0000-0003-2653-0395
0000-0001-8514-7471
0000-0002-3740-7424
0000-0002-5600-9886
PMID 28378382
PQID 1888859370
PQPubID 946352
PageCount 5
ParticipantIDs webofscience_primary_000399384700008CitationCount
proquest_miscellaneous_1884472505
proquest_journals_1888859370
crossref_primary_10_1002_anie_201610699
wiley_primary_10_1002_anie_201610699_ANIE201610699
proquest_journals_1905736114
pubmed_primary_28378382
webofscience_primary_000399384700008
crossref_citationtrail_10_1002_anie_201610699
ProviderPackageCode CITATION
AAYXX
PublicationCentury 2000
PublicationDate April 24, 2017
PublicationDateYYYYMMDD 2017-04-24
PublicationDate_xml – month: 04
  year: 2017
  text: April 24, 2017
  day: 24
PublicationDecade 2010
PublicationPlace WEINHEIM
PublicationPlace_xml – name: WEINHEIM
– name: Germany
– name: Weinheim
PublicationTitle Angewandte Chemie International Edition
PublicationTitleAbbrev ANGEW CHEM INT EDIT
PublicationTitleAlternate Angew Chem Int Ed Engl
PublicationYear 2017
Publisher Wiley
Wiley Subscription Services, Inc
Publisher_xml – name: Wiley
– name: Wiley Subscription Services, Inc
References 2010; 15
2000; 43
2013; 62
2014; 25
1999; 42
2007; 72
2008; 6
2015; 80
2008; 73
2007; 37
1955; 88
1977; 60
2014; 20
2009; 11
2014; 4
2006; 62
2013; 11
2009; 50
1999; 16
2014; 16
2005; 70
1953; 583
2014; 50
1975; 108
2014; 10
2015; 17
2015; 6
2013; 43
2015; 51
2010
2004; 47
2008; 18
2002; 32
2009
1998
1997; 29
2006; 8
1997
1992; 35
2008; 10
2007; 11
2012; 77
2009; 74
2012; 354
2010; 46
2013; 78
1980; 2
1964; 97
2016
2015
1994; 59
2005; 3
2007; 48
1953; 86
1972; 37
e_1_2_2_24_2
e_1_2_2_47_2
Zvilichovsky G. (e_1_2_2_53_1) 2010
e_1_2_2_4_2
e_1_2_2_22_2
e_1_2_2_49_2
e_1_2_2_6_2
e_1_2_2_2_2
e_1_2_2_62_1
e_1_2_2_41_2
e_1_2_2_64_1
e_1_2_2_8_2
e_1_2_2_28_2
e_1_2_2_43_2
e_1_2_2_66_1
e_1_2_2_26_2
e_1_2_2_45_2
e_1_2_2_68_1
e_1_2_2_60_2
e_1_2_2_13_2
e_1_2_2_59_2
e_1_2_2_11_2
e_1_2_2_38_2
e_1_2_2_51_2
e_1_2_2_19_2
e_1_2_2_30_2
e_1_2_2_17_2
e_1_2_2_32_2
e_1_2_2_55_1
e_1_2_2_15_2
e_1_2_2_34_2
e_1_2_2_36_1
e_1_2_2_57_1
Schwartz C. (e_1_2_2_20_2) 2009
e_1_2_2_3_2
e_1_2_2_23_2
e_1_2_2_48_2
e_1_2_2_5_2
e_1_2_2_21_2
e_1_2_2_1_1
e_1_2_2_63_1
e_1_2_2_40_2
e_1_2_2_61_2
e_1_2_2_65_1
e_1_2_2_29_2
e_1_2_2_42_2
e_1_2_2_7_2
e_1_2_2_44_1
e_1_2_2_67_1
e_1_2_2_27_2
e_1_2_2_9_2
e_1_2_2_25_2
McCullough K. J. (e_1_2_2_46_2) 1980; 2
e_1_2_2_12_2
e_1_2_2_37_2
e_1_2_2_58_2
e_1_2_2_10_2
e_1_2_2_39_2
e_1_2_2_31_1
e_1_2_2_54_1
e_1_2_2_18_2
e_1_2_2_52_2
e_1_2_2_56_1
e_1_2_2_33_2
e_1_2_2_16_1
e_1_2_2_14_2
e_1_2_2_35_2
e_1_2_2_50_1
Liu, YH (WOS:000300448400024) 2012; 354
Tada, N (WOS:000274827000055) 2010; 46
Kim, HS (WOS:000081532500011) 1999; 42
Kyasa, S (WOS:000317327800075) 2013; 78
Novikov, VL (WOS:000339728300010) 2013; 62
Zvilichovsky, G. (000399384700008.61) 1993
Zmitek, K (WOS:000237951800012) 2006; 8
Klapötke, TM (WOS:000362747900013) 2015; 2015
Chaudhary, S (WOS:000363225000005) 2015; 17
Terent'ev, AO (WOS:000329820200001) 2014; 10
VENNERSTROM, JL (WOS:A1992JH46900015) 1992; 35
Azarifar, D (WOS:000269084500013) 2009
Bunge, A (WOS:000263383600006) 2009; 50
CRIEGEE, R (WOS:A1953UL03000001) 1953; 86
CRIEGEE, R (WOS:A1953XV10200001) 1953; 583
Najjar, F (WOS:000228719200017) 2005; 3
Griesbaum, K (WOS:000073002600009) 1998; 1998
GRAY, RW (WOS:A1977DU95300017) 1977; 60
Ghorai, P (WOS:000259940600047) 2008; 10
Alabugin, I. V. (000399384700008.1) 2016
Yaremenko, IA (WOS:000340257000042) 2014; 20
KONDELIKOVA, J (WOS:A1972L760900027) 1972; 37
Casteel, DA (WOS:000078574000005) 1999; 16
Martyn, DC (WOS:000261141100050) 2008; 18
Ellis, GL (WOS:000254180200035) 2008; 18
Terent'ev, AO (WOS:000249371200020) 2007; 72
Schwartz, C. (000399384700008.43) 2009
Terent'ev, AO (WOS:000261744800021) 2008; 6
Zmitek, K (WOS:000235123900019) 2006; 62
CRIEGEE, R (WOS:A1955WK06600009) 1955; 88
Chung, A (WOS:000347506400029) 2015; 80
RIECHE, A (WOS:A19648532A00024) 1964; 97
JEFFORD CW (WOS:000399384700008.24) 1997; 29
Prakash, GKS (WOS:000338298600027) 2014; 16
Yadav, N (WOS:000329579900023) 2014; 4
McCullough, K. J. (000399384700008.37) 1980; 2
Terent'ev, AO (WOS:000247620500026) 2007; 37
MAYR, H (WOS:A1994PE44300059) 1994; 59
Das, B (WOS:000249216800011) 2007; 48
Gilmore, K (WOS:000342990400013) 2014; 50
Gomes, GD (WOS:000365225300011) 2015; 6
CRIEGEE, R (WOS:A1975AB79300032) 1975; 108
Zmitek, K (WOS:000248793400026) 2007; 72
Gelb, MH (WOS:000249682700015) 2007; 11
Borstnik, K (WOS:000179898500016) 2002; 32
Li, Y (WOS:000264622600054) 2009; 11
Kandur, WV (WOS:000336199200020) 2014; 16
Terent'ev, AO (WOS:000368737400002) 2015; 51
McCullough, KJ (WOS:000086055900023) 2000; 43
van Tonder, JH (WOS:000338110700033) 2014; 25
Lau, SH (WOS:000357623900008) 2015; 17
O'Neill, PM (WOS:000221740900001) 2004; 47
Terent'ev, AO (WOS:000265554900013) 2009; 74
Terent'ev, AO (WOS:000316803900010) 2013; 11
Azarifar, D (WOS:000312599700006) 2013; 43
Kvasnica, M (WOS:000232832300009) 2005; 70
Griesbaum, K (WOS:A1997XK28000013) 1997
Azarifar, D (WOS:000275956900027) 2010; 15
Terent'ev, AO (WOS:000300340000021) 2012; 77
Terent'ev, AO (WOS:000254883700022) 2008; 73
Ghorai, P (WOS:000262018700054) 2009; 11
References_xml – volume: 20
  start-page: 10160
  year: 2014
  end-page: 10169
  publication-title: Chem. Eur. J.
– year: 2009
– volume: 3
  start-page: 1612
  year: 2005
  end-page: 1614
  publication-title: Org. Biomol. Chem.
– volume: 72
  start-page: 7237
  year: 2007
  end-page: 7243
  publication-title: J. Org. Chem.
– volume: 354
  start-page: 441
  year: 2012
  end-page: 447
  publication-title: Adv. Synth. Catal.
– start-page: 2553
  year: 2009
  end-page: 2556
  publication-title: Synthesis
– volume: 11
  start-page: 1615
  year: 2009
  end-page: 1618
  publication-title: Org. Lett.
– volume: 10
  start-page: 4577
  year: 2008
  end-page: 4579
  publication-title: Org. Lett.
– volume: 583
  start-page: 1
  year: 1953
  end-page: 36
  publication-title: Justus Liebigs Ann. Chem.
– volume: 32
  start-page: 1661
  year: 2002
  end-page: 1667
  publication-title: Int. J. Parasitol.
– volume: 8
  start-page: 2491
  year: 2006
  end-page: 2494
  publication-title: Org. Lett.
– volume: 51
  start-page: 1681
  year: 2015
  end-page: 1687
  publication-title: Russ. J. Org. Chem.
– volume: 47
  start-page: 2945
  year: 2004
  end-page: 2964
  publication-title: J. Med. Chem.
– volume: 16
  start-page: 2650
  year: 2014
  end-page: 2653
  publication-title: Org. Lett.
– volume: 60
  start-page: 1969
  year: 1977
  end-page: 1979
  publication-title: Helv. Chim. Acta
– volume: 25
  start-page: 1629
  year: 2014
  end-page: 1630
  publication-title: Synlett
– volume: 6
  start-page: 4435
  year: 2008
  end-page: 4441
  publication-title: Org. Biomol. Chem.
– volume: 18
  start-page: 1720
  year: 2008
  end-page: 1724
  publication-title: Bioorg. Med. Chem. Lett.
– volume: 86
  start-page: 1
  year: 1953
  end-page: 4
  publication-title: Chem. Ber.
– volume: 62
  start-page: 1479
  year: 2006
  end-page: 1484
  publication-title: Tetrahedron
– volume: 42
  start-page: 2604
  year: 1999
  end-page: 2609
  publication-title: J. Med. Chem.
– volume: 16
  start-page: 55
  year: 1999
  end-page: 73
  publication-title: Nat. Prod. Rep.
– volume: 46
  start-page: 1772
  year: 2010
  end-page: 1774
  publication-title: Chem. Commun.
– volume: 74
  start-page: 3335
  year: 2009
  end-page: 3340
  publication-title: J. Org. Chem.
– volume: 88
  start-page: 1878
  year: 1955
  end-page: 1888
  publication-title: Chem. Ber.
– volume: 15
  start-page: 1433
  year: 2010
  publication-title: Molecules
– volume: 73
  start-page: 3169
  year: 2008
  end-page: 3174
  publication-title: J. Org. Chem.
– volume: 10
  start-page: 34
  year: 2014
  end-page: 114
  publication-title: Beilstein J. Org. Chem.
– start-page: 1381
  year: 1997
  end-page: 1390
  publication-title: Liebigs Ann.
– volume: 6
  start-page: 6783
  year: 2015
  end-page: 6791
  publication-title: Chem. Sci.
– volume: 4
  start-page: 5469
  year: 2014
  end-page: 5498
  publication-title: RSC Adv.
– volume: 108
  start-page: 1642
  year: 1975
  end-page: 1654
  publication-title: Chem. Ber.
– volume: 29
  start-page: 271
  year: 1997
  end-page: 325
  publication-title: Adv. Drug Res.
– volume: 59
  start-page: 5055
  year: 1994
  end-page: 5058
  publication-title: J. Org. Chem.
– volume: 17
  start-page: 3218
  year: 2015
  end-page: 3221
  publication-title: Org. Lett.
– volume: 62
  start-page: 2171
  year: 2013
  end-page: 2190
  publication-title: Russ. Chem. Bull.
– start-page: 687
  year: 2010
  end-page: 784
– start-page: 627
  year: 1998
  end-page: 629
  publication-title: Eur. J. Org. Chem.
– volume: 35
  start-page: 3023
  year: 1992
  end-page: 3027
  publication-title: J. Med. Chem.
– volume: 72
  start-page: 6534
  year: 2007
  end-page: 6540
  publication-title: J. Org. Chem.
– volume: 11
  start-page: 213
  year: 2009
  end-page: 216
  publication-title: Org. Lett.
– year: 2016
– volume: 37
  start-page: 1281
  year: 2007
  end-page: 1287
  publication-title: Synth. Commun.
– volume: 43
  start-page: 1246
  year: 2000
  end-page: 1249
  publication-title: J. Med. Chem.
– volume: 43
  start-page: 826
  year: 2013
  end-page: 836
  publication-title: Synth. Commun.
– volume: 2
  start-page: 601
  year: 1980
  end-page: 628
  publication-title: J. Chem. Res. Miniprint
– volume: 16
  start-page: 3616
  year: 2014
  end-page: 3622
  publication-title: Green Chem.
– volume: 78
  start-page: 3452
  year: 2013
  end-page: 3456
  publication-title: J. Org. Chem.
– start-page: 6237
  year: 2015
  end-page: 6242
  publication-title: Eur. J. Org. Chem.
– volume: 77
  start-page: 1833
  year: 2012
  end-page: 1842
  publication-title: J. Org. Chem.
– volume: 70
  start-page: 1447
  year: 2005
  end-page: 1464
  publication-title: Collect. Czech. Chem. Commun.
– volume: 18
  start-page: 6521
  year: 2008
  end-page: 6524
  publication-title: Bioorg. Med. Chem. Lett.
– volume: 11
  start-page: 2613
  year: 2013
  end-page: 2623
  publication-title: Org. Biomol. Chem.
– volume: 50
  start-page: 524
  year: 2009
  end-page: 526
  publication-title: Tetrahedron Lett.
– volume: 17
  start-page: 4948
  year: 2015
  end-page: 4951
  publication-title: Org. Lett.
– volume: 37
  start-page: 263
  year: 1972
  end-page: 269
  publication-title: Collect. Czech. Chem. Commun.
– volume: 50
  start-page: 12652
  year: 2014
  end-page: 12655
  publication-title: Chem. Commun.
– volume: 97
  start-page: 3071
  year: 1964
  end-page: 3075
  publication-title: Chem. Ber.
– volume: 11
  start-page: 440
  year: 2007
  end-page: 445
  publication-title: Curr. Opin. Chem. Biol.
– volume: 48
  start-page: 6286
  year: 2007
  end-page: 6289
  publication-title: Tetrahedron Lett.
– volume: 80
  start-page: 266
  year: 2015
  end-page: 273
  publication-title: J. Org. Chem.
– ident: e_1_2_2_41_2
  doi: 10.1039/c3ra42513d
– ident: e_1_2_2_62_1
  doi: 10.1002/cber.19530860102
– ident: e_1_2_2_27_2
  doi: 10.1055/s-0034-1378210
– ident: e_1_2_2_54_1
  doi: 10.1002/jlac.199719970715
– ident: e_1_2_2_32_2
  doi: 10.1021/jo0708745
– ident: e_1_2_2_38_2
  doi: 10.1039/c3ob27239g
– ident: e_1_2_2_52_2
  doi: 10.1134/S1070428015120027
– ident: e_1_2_2_7_2
  doi: 10.1021/jm00094a015
– ident: e_1_2_2_10_2
  doi: 10.1039/a705725c
– ident: e_1_2_2_47_2
  doi: 10.1016/j.tet.2005.11.022
– ident: e_1_2_2_63_1
  doi: 10.1135/cccc19720263
– ident: e_1_2_2_64_1
  doi: 10.1002/hlca.19770600618
– ident: e_1_2_2_30_2
  doi: 10.1016/j.tetlet.2007.07.012
– ident: e_1_2_2_51_2
  doi: 10.1021/jo202437r
– ident: e_1_2_2_23_2
  doi: 10.3390/molecules15031433
– ident: e_1_2_2_22_2
  doi: 10.1016/j.tetlet.2008.11.055
– ident: e_1_2_2_31_1
– ident: e_1_2_2_39_2
  doi: 10.1021/ol8023874
– ident: e_1_2_2_35_2
  doi: 10.1021/ol500835f
– ident: e_1_2_2_58_2
  doi: 10.1002/jlac.19535830102
– ident: e_1_2_2_36_1
– ident: e_1_2_2_13_2
  doi: 10.1016/j.bmcl.2008.01.053
– ident: e_1_2_2_45_2
  doi: 10.1002/cber.19640971116
– ident: e_1_2_2_24_2
  doi: 10.1039/b917056a
– ident: e_1_2_2_34_2
  doi: 10.1021/jo4001564
– ident: e_1_2_2_68_1
  doi: 10.1002/chem.201402594
– ident: e_1_2_2_67_1
  doi: 10.1021/acs.orglett.5b02296
– ident: e_1_2_2_44_1
– ident: e_1_2_2_55_1
  doi: 10.1039/C5SC02402A
– ident: e_1_2_2_21_2
  doi: 10.1021/ol900262t
– volume: 2
  start-page: 601
  year: 1980
  ident: e_1_2_2_46_2
  publication-title: J. Chem. Res. Miniprint
– ident: e_1_2_2_14_2
  doi: 10.1016/j.bmcl.2008.10.083
– ident: e_1_2_2_1_1
– ident: e_1_2_2_57_1
– ident: e_1_2_2_28_2
  doi: 10.1039/c4gc00586d
– start-page: 687
  volume-title: Hydroxyl, Ether and Peroxide Groups (1993)
  year: 2010
  ident: e_1_2_2_53_1
– ident: e_1_2_2_56_1
  doi: 10.1002/9781118906378
– ident: e_1_2_2_2_2
  doi: 10.1016/S0065-2490(97)80016-0
– ident: e_1_2_2_48_2
  doi: 10.1021/jo071072c
– ident: e_1_2_2_59_2
  doi: 10.1002/cber.19550881210
– ident: e_1_2_2_9_2
  doi: 10.1021/jm990014j
– ident: e_1_2_2_18_2
  doi: 10.1080/00397910701226384
– ident: e_1_2_2_4_2
  doi: 10.1021/jo502344x
– volume-title: Patai's Chemistry of Functional Groups
  year: 2009
  ident: e_1_2_2_20_2
– ident: e_1_2_2_40_2
  doi: 10.1007/s11172-013-0316-6
– ident: e_1_2_2_50_1
– ident: e_1_2_2_15_2
  doi: 10.1021/acs.orglett.5b01307
– ident: e_1_2_2_26_2
  doi: 10.1080/00397911.2011.610549
– ident: e_1_2_2_33_2
  doi: 10.1039/b809661a
– ident: e_1_2_2_17_2
  doi: 10.1021/ol060590r
– ident: e_1_2_2_11_2
  doi: 10.1021/jm990530
– ident: e_1_2_2_3_2
  doi: 10.1021/jm030571c
– ident: e_1_2_2_6_2
  doi: 10.1016/S0020-7519(02)00195-9
– ident: e_1_2_2_49_2
  doi: 10.1021/jo7027213
– ident: e_1_2_2_42_2
  doi: 10.3762/bjoc.10.6
– ident: e_1_2_2_19_2
  doi: 10.1021/ol801859c
– ident: e_1_2_2_61_2
  doi: 10.1021/jo00096a059
– ident: e_1_2_2_8_2
  doi: 10.1016/j.cbpa.2007.05.038
– ident: e_1_2_2_29_2
  doi: 10.1055/s-0029-1217394
– ident: e_1_2_2_66_1
  doi: 10.1002/(SICI)1099-0690(199804)1998:4<627::AID-EJOC627>3.0.CO;2-N
– ident: e_1_2_2_37_2
  doi: 10.1021/jo900226b
– ident: e_1_2_2_12_2
  doi: 10.1039/b503402g
– ident: e_1_2_2_16_1
– ident: e_1_2_2_5_2
  doi: 10.1039/C4CC05098C
– ident: e_1_2_2_43_2
  doi: 10.1002/ejoc.201500919
– ident: e_1_2_2_65_1
  doi: 10.1135/cccc20051447
– ident: e_1_2_2_25_2
  doi: 10.1002/adsc.201100561
– ident: e_1_2_2_60_2
  doi: 10.1002/cber.19751080533
– volume: 3
  start-page: 1612
  year: 2005
  ident: WOS:000228719200017
  article-title: Alkylation of natural endoperoxide G3-factor.: Synthesis and antimalarial activity studies
  publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY
  doi: 10.1039/b503402g
– volume: 2
  start-page: 601
  year: 1980
  ident: 000399384700008.37
  publication-title: J. Chem. Res. Miniprint
– volume: 80
  start-page: 266
  year: 2015
  ident: WOS:000347506400029
  article-title: Formation of an Endoperoxide upon Chromium-Catalyzed Allylic Oxidation of a Triterpene by Oxygen
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
– volume: 25
  start-page: 1629
  year: 2014
  ident: WOS:000338110700033
  article-title: gem-Bishydroperoxides
  publication-title: SYNLETT
  doi: 10.1055/s-0034-1378210
– volume: 70
  start-page: 1447
  year: 2005
  ident: WOS:000232832300009
  article-title: Preparation of new oxidized 18-α-oleanane derivatives
  publication-title: COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
  doi: 10.1135/cccc20051447
– volume: 50
  start-page: 12652
  year: 2014
  ident: WOS:000342990400013
  article-title: Continuous synthesis of artemisinin-derived medicines
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/c4cc05098c
– volume: 74
  start-page: 3335
  year: 2009
  ident: WOS:000265554900013
  article-title: Facile and Selective Procedure for the Synthesis of Bridged 1,2,4,5-Tetraoxanes; Strong Acids As Cosolvents and Catalysts for Addition of Hydrogen Peroxide to β-Diketones
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo900226b
– volume: 11
  start-page: 440
  year: 2007
  ident: WOS:000249682700015
  article-title: Drug discovery for malaria: a very challenging and timely endeavor
  publication-title: CURRENT OPINION IN CHEMICAL BIOLOGY
  doi: 10.1016/j.cbpa.2007.05.038
– volume: 77
  start-page: 1833
  year: 2012
  ident: WOS:000300340000021
  article-title: Selective Synthesis of Cyclic Peroxides from Triketones and H2O2
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo202437r
– volume: 72
  start-page: 7237
  year: 2007
  ident: WOS:000249371200020
  article-title: New preparation of 1,2,4,5,7,8-hexaoxonanes
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo071072c
– volume: 108
  start-page: 1642
  year: 1975
  ident: WOS:A1975AB79300032
  article-title: INTRAMOLECULAR COMPETITION DURING OZONOLYSIS OF SUBSTITUTED CYCLOPENTENES
  publication-title: CHEMISCHE BERICHTE-RECUEIL
– volume: 29
  start-page: 271
  year: 1997
  ident: WOS:000399384700008.24
  publication-title: ADV DRUG RES
– volume: 48
  start-page: 6286
  year: 2007
  ident: WOS:000249216800011
  article-title: A simple and efficient synthesis of gem-dihydroperoxides from ketones using aqueous hydrogen peroxide and catalytic ceric ammonium nitrate
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2007.07.012
– volume: 35
  start-page: 3023
  year: 1992
  ident: WOS:A1992JH46900015
  article-title: DISPIRO-1,2,4,5-TETRAOXANES - A NEW CLASS OF ANTIMALARIAL PEROXIDES
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
– volume: 59
  start-page: 5055
  year: 1994
  ident: WOS:A1994PE44300059
  article-title: EXCEPTIONALLY STABLE OZONIDES - INFLUENCE OF METHYL SUBSTITUENTS ON THE COURSE OF CYCLOPENTENE OZONOLYSES AND ON THE REACTIVITIES OF OZONIDES
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
– volume: 42
  start-page: 2604
  year: 1999
  ident: WOS:000081532500011
  article-title: Synthesis and antimalarial activity of cyclic peroxides, 1,2,4,5,7-pentoxocanes and 1,2,4,5-tetroxanes
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
– volume: 78
  start-page: 3452
  year: 2013
  ident: WOS:000317327800075
  article-title: Synthesis of Alkyl Hydroperoxides via Alkylation of gem-Dihydroperoxides
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo4001564
– volume: 37
  start-page: 1281
  year: 2007
  ident: WOS:000247620500026
  article-title: Convenient synthesis of geminal bishydroperoxides by the reaction of ketones with hydrogen peroxide
  publication-title: SYNTHETIC COMMUNICATIONS
  doi: 10.1080/00397910701226384
– volume: 62
  start-page: 1479
  year: 2006
  ident: WOS:000235123900019
  article-title: Fluorinated alcohol directed formation of dispiro-1,2,4,5-tetraoxanes by hydrogen peroxide under acid conditions
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2005.11.022
– year: 2016
  ident: 000399384700008.1
  publication-title: Stereoelectronic Effects: The Bridge between Structure and Reactivity
– volume: 32
  start-page: 1661
  year: 2002
  ident: WOS:000179898500016
  article-title: Antimalarial chemotherapeutic peroxides: artemisinin, yingzhaosu A and related compounds
  publication-title: INTERNATIONAL JOURNAL FOR PARASITOLOGY
– start-page: 687
  year: 1993
  ident: 000399384700008.61
  publication-title: Hydroxyl
– volume: 18
  start-page: 1720
  year: 2008
  ident: WOS:000254180200035
  article-title: An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2008.01.053
– volume: 6
  start-page: 4435
  year: 2008
  ident: WOS:000261744800021
  article-title: Synthesis of 1-hydroperoxy-1′-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers
  publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY
  doi: 10.1039/b809661a
– volume: 17
  start-page: 3218
  year: 2015
  ident: WOS:000357623900008
  article-title: Machines vs Malaria: A Flow-Based Preparation of the Drug Candidate OZ439
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.5b01307
– volume: 47
  start-page: 2945
  year: 2004
  ident: WOS:000221740900001
  article-title: A medicinal chemistry perspective on artemisinin and related endoperoxides
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1021/jm030571c
– start-page: 1381
  year: 1997
  ident: WOS:A1997XK28000013
  article-title: Ozonolyses of O-alkylated ketoximes in the presence of carbonyl groups: A facile access to ozonides
  publication-title: LIEBIGS ANNALEN-RECUEIL
– volume: 37
  start-page: 263
  year: 1972
  ident: WOS:A1972L760900027
  article-title: REACTIONS OF 2,2'-METHYLENE-BIS (CYCLOHEXANONE) WITH HYDROGEN-PEROXIDE AND PEROXY ACIDS
  publication-title: COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
– year: 2009
  ident: 000399384700008.43
  publication-title: Patai Q s Chemistry of Functional Groups
– volume: 51
  start-page: 1681
  year: 2015
  ident: WOS:000368737400002
  article-title: Synthesis of peroxides from β,δ-triketones under heterogeneous conditions
  publication-title: RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1134/S1070428015120027
– volume: 43
  start-page: 1246
  year: 2000
  ident: WOS:000086055900023
  article-title: Methyl-substituted dispiro-1,2,4,5-tetraoxanes: Correlations of structural studies with antimalarial activity
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
– volume: 50
  start-page: 524
  year: 2009
  ident: WOS:000263383600006
  article-title: A simple, efficient and versatile synthesis of primary gem-dihydroperoxides from aldehydes and hydrogen peroxide
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2008.11.055
– volume: 16
  start-page: 55
  year: 1999
  ident: WOS:000078574000005
  article-title: Peroxy natural products
  publication-title: NATURAL PRODUCT REPORTS
– volume: 97
  start-page: 3071
  year: 1964
  ident: WOS:A19648532A00024
  article-title: ALKYLPEROXYDE .35. PEROXYDE DES TRIACETYLMETHANS TRIACETYLMETHANPEROXYD
  publication-title: CHEMISCHE BERICHTE-RECUEIL
– volume: 17
  start-page: 4948
  year: 2015
  ident: WOS:000363225000005
  article-title: Stable Tricyclic Antitubercular Ozonides Derived from Artemisinin
  publication-title: ORGANIC LETTERS
  doi: 10.1021/acs.orglett.5b02296
– volume: 4
  start-page: 5469
  year: 2014
  ident: WOS:000329579900023
  article-title: Diversification in the synthesis of antimalarial trioxane and tetraoxane analogs
  publication-title: RSC ADVANCES
  doi: 10.1039/c3ra42513d
– volume: 16
  start-page: 3616
  year: 2014
  ident: WOS:000338298600027
  article-title: Poly(N-vinylpyrrolidone)-H2O2 and poly(4-vinylpyridine)-H2O2 complexes: solid H2O2 equivalents for selective oxidation of sulfides to sulfoxides and ketones to gem-dihydroperoxides
  publication-title: GREEN CHEMISTRY
  doi: 10.1039/c4gc00586d
– volume: 62
  start-page: 2171
  year: 2013
  ident: WOS:000339728300010
  article-title: Reactions of hydrogen peroxide with acetylacetone and 2-acetylcyclopentanone
  publication-title: RUSSIAN CHEMICAL BULLETIN
  doi: 10.1007/s11172-013-0316-6
– volume: 18
  start-page: 6521
  year: 2008
  ident: WOS:000261141100050
  article-title: Synthesis of spiro-1,2-dioxolanes and their activity against Plasmodium falciparum
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2008.10.083
– volume: 2015
  start-page: 6237
  year: 2015
  ident: WOS:000362747900013
  article-title: Energetic Organic Peroxides - Synthesis and Characterization of 1,4-Dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptanes
  publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1002/ejoc.201500919
– volume: 583
  start-page: 1
  year: 1953
  ident: WOS:A1953XV10200001
  article-title: *UBER DEN VERLAUF DER OZONSPALTUNG .3.
  publication-title: ANNALEN DER CHEMIE-JUSTUS LIEBIG
– volume: 46
  start-page: 1772
  year: 2010
  ident: WOS:000274827000055
  article-title: A facile catalyst-free synthesis of gem-dihydroperoxides with aqueous hydrogen peroxide
  publication-title: CHEMICAL COMMUNICATIONS
  doi: 10.1039/b917056a
– volume: 11
  start-page: 213
  year: 2009
  ident: WOS:000262018700054
  article-title: Broadly Applicable Synthesis of-1,2,4,5-Tetraoxanes.
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol8023874
– volume: 43
  start-page: 826
  year: 2013
  ident: WOS:000312599700006
  article-title: Synthesis of gem-Dihydroperoxides from Ketones and Aldehydes Using Silica Sulfuric Acid as Heterogeneous Reusable Catalyst
  publication-title: SYNTHETIC COMMUNICATIONS
  doi: 10.1080/00397911.2011.610549
– volume: 88
  start-page: 1878
  year: 1955
  ident: WOS:A1955WK06600009
  article-title: DER BILDUNGSBEREICH MONOMERER OZONIDE
  publication-title: CHEMISCHE BERICHTE-RECUEIL
– volume: 15
  start-page: 1433
  year: 2010
  ident: WOS:000275956900027
  article-title: Mild and Efficient Strontium Chloride Hexahydrate-Catalyzed Conversion of Ketones and Aldehydes into Corresponding gem-Dihydroperoxides by Aqueous H2O2
  publication-title: MOLECULES
  doi: 10.3390/molecules15031433
– volume: 8
  start-page: 2491
  year: 2006
  ident: WOS:000237951800012
  article-title: Iodine as a catalyst for efficient conversion of ketones to gem-dihydroperoxides by aqueous hydrogen peroxide
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol060590r
– volume: 16
  start-page: 2650
  year: 2014
  ident: WOS:000336199200020
  article-title: Synthesis and Reactivity of 1,2-Dioxolanes from β,γ-Epoxy Ketones
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol500835f
– volume: 11
  start-page: 2613
  year: 2013
  ident: WOS:000316803900010
  article-title: Phosphomolybdic and phosphotungstic acids as efficient catalysts for the synthesis of bridged 1,2,4,5-tetraoxanes from β-diketones and hydrogen peroxide
  publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY
  doi: 10.1039/c3ob27239g
– volume: 6
  start-page: 6783
  year: 2015
  ident: WOS:000365225300011
  article-title: Stereoelectronic source of the anomalous stability of bis-peroxides
  publication-title: CHEMICAL SCIENCE
  doi: 10.1039/c5sc02402a
– volume: 60
  start-page: 1969
  year: 1977
  ident: WOS:A1977DU95300017
  article-title: FORMATION OF CYCLOPENTADECANE-1,5-DIONE DERIVATIVES BY AN OXIRANYLMETHYL FRAGMENTATION - SYNTHESIS OF MUSCONE
  publication-title: HELVETICA CHIMICA ACTA
– start-page: 2553
  year: 2009
  ident: WOS:000269084500013
  article-title: Stannous Chloride Dihydrate: A Novel and Efficient Catalyst for the Synthesis of gem-Dihydroperoxides from Ketones and Aldehydes
  publication-title: SYNTHESIS-STUTTGART
  doi: 10.1055/s-0029-1217394
– volume: 354
  start-page: 441
  year: 2012
  ident: WOS:000300448400024
  article-title: Triflic Acid-Functionalized Silica-Coated Magnetic Nanoparticles as a Magnetically Separable Catalyst for Synthesis of gem-Dihydroperoxides
  publication-title: ADVANCED SYNTHESIS & CATALYSIS
  doi: 10.1002/adsc.201100561
– volume: 10
  start-page: 4577
  year: 2008
  ident: WOS:000259940600047
  article-title: Mild and Efficient Re(VII)-Catalyzed Synthesis of 1,1-Dihydroperoxides
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol801859c
– volume: 20
  start-page: 10160
  year: 2014
  ident: WOS:000340257000042
  article-title: Approach for the Preparation of Various Classes of Peroxides Based on the Reaction of Triketones with H2O2: First Examples of Ozonide Rearrangements
  publication-title: CHEMISTRY-A EUROPEAN JOURNAL
  doi: 10.1002/chem.201402594
– volume: 1998
  start-page: 627
  year: 1998
  ident: WOS:000073002600009
  article-title: Gas-phase reactions of 1,2-dimethylcyclopentene and of 2,6-heptanedione with ozone: Unprecedented formation of an ozonide by ozone treatment of a diketone
  publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
– volume: 86
  start-page: 1
  year: 1953
  ident: WOS:A1953UL03000001
  article-title: UBER DAS OZONID DES 1.2-DIMETHYL-CYCLOPENTENS-(1) .2. UBER DEN VERLAUF DER OZONSPALTUNG
  publication-title: CHEMISCHE BERICHTE-RECUEIL
– volume: 72
  start-page: 6534
  year: 2007
  ident: WOS:000248793400026
  article-title: The effect of iodine on the peroxidation of carbonyl compounds
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo0708745
– volume: 11
  start-page: 1615
  year: 2009
  ident: WOS:000264622600054
  article-title: A Broadly Applicable Mild Method for the Synthesis of gem-Diperoxides from Corresponding Ketones or 1,3-Dioxolanes
  publication-title: ORGANIC LETTERS
  doi: 10.1021/ol900262t
– volume: 10
  start-page: 34
  year: 2014
  ident: WOS:000329820200001
  article-title: Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products
  publication-title: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.3762/bjoc.10.6
– volume: 73
  start-page: 3169
  year: 2008
  ident: WOS:000254883700022
  article-title: Synthesis of cyclic peroxides containing the Si-gem-bisperoxide fragment. 1,2,4,5,7,8-hexaoxa-3-silonanes as a new class of Peroxides
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo7027213
SSID ssj0028806
Score 2.4201374
Snippet The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone‐free synthesis of bridged secondary ozonides from...
The value of stereoelectronic guidelines is illustrated by the discovery of a convenient, ozone-free synthesis of bridged secondary ozonides from...
Source Web of Science
SourceID proquest
pubmed
webofscience
crossref
wiley
SourceType Aggregation Database
Index Database
Enrichment Source
Publisher
StartPage 4955
SubjectTerms anomeric effect
Carbon
Carbonyl compounds
Carbonyls
Chemistry
Chemistry, Multidisciplinary
Deactivation
Distortion
Guidelines
Hydrogen peroxide
Ozone
Ozonides
peroxides
Physical Sciences
Science & Technology
stereoelectronic control
synthetic methods
Title Stereoelectronic Control in the Ozone‐Free Synthesis of Ozonides
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201610699
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000399384700008
https://www.ncbi.nlm.nih.gov/pubmed/28378382
https://www.proquest.com/docview/1888859370
https://www.proquest.com/docview/1905736114
https://www.proquest.com/docview/1884472505
Volume 56
WOS 000399384700008
WOSCitedRecordID wos000399384700008
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1LT9wwEB5VXNpLX_QRXgoSUk-GxHa8yZGuWFEkQIIicYv8irQqyiKyeyin_oT-Rn5JZ5wHLG3Vqs0t8TjxY5z5nMx8A7CDkD4zlUsYN9YziXsQZnxqmcmkK3SFBjkE0h6fqMMLeXSZXT6I4m_5IYYPbrQywvuaFrg2zd49aShFYJNrFtp_VVAEHzlsESo6G_ijOCpnG14kBKMs9D1rY8L3lqsvW6WfoOYjq7QMZIMlmrwA3fehdUD5sruYm117-4je8X86-RKedzA13m_16hU88fVreDrus8OtwsdznBA_u8-iE49bp_d4WscIKuPT21nt7759n9x4H59_rfFaM23iWRVKps43b-BicvB5fMi6fAzMUo50ljmHmx098qqwIjeV5uTNmeRaO0ENrArLrVeWQGXmUl_knNCAy3JjleNKvIWVGp_9HmIlndUi82IkUqmtMpqiYlE-cV7q1EbA-vkobUdWTjkzrsqWZpmXNDLlMDIRfBjkr1uajt9KbvTTW3bLtSnTHI8MkVry6-KCaCMVbh0j2B6KccDp54qu_WwRbiHliABlBO9arRlaQgxDuch5BDsP1WgoDxHShUCgECB8BOnfiI27cSHygnkEPOjRH3pf7p98OhjO1v6l0jo84wRtEsm43ICV-c3CbyIwm5utsPh-AAV7LPc
linkProvider Wiley-Blackwell
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lb9QwEB5BOZQLlFcJFAhSJU5uE9vxJsey6moL7SLRVuIW-RVpBcqi7u6BnvgJ_Mb-ks44j3YLCAS5JZ4k9ngcf3ZmvgHYRkifmcoljBvrmcQ1CDM-tcxk0hW6wgk5BNIeTdT4VL77lHXehBQL0_BD9BtuNDLC95oGOG1I716xhlIINvlmIQBQRXEb7lBa77Cq-tgzSHE0zybASAhGeeg73saE767evzov_QQ2b8xLq1A2zEWj-2C6VjQuKJ93lguzY89vEDz-VzM34F6LVOO9xrQewC1fP4T1YZcg7hG8PcY-8bOrRDrxsPF7j6d1jLgy_nA-q_3F9x-jM-_j4281XptP5_GsCiVT5-eP4XS0fzIcszYlA7OUJp1lzuF6Rw-8KqzITaU5OXQmudZOUAWrwnLrlSVcmbnUFzknQOCy3FjluBJPYK3Gdz-FWElntci8GIhUaquMpsBYlE-clzq1EbCuQ0rb8pVT2owvZcO0zEvSTNlrJoI3vfzXhqnjt5JbXf-W7Yidl2mOR4ZgLfl1cUHMkQpXjxG87otR4fR_Rdd-tgyPkHJAmDKCzcZs-poQyVAuch7B9nU76stDkHQhECsEFB9B-jdiw1YvxF-wiIAHQ_pD68u9ycF-f_bsX256Bevjk6PD8vBg8v453OWEdBLJuNyCtcXZ0r9AnLYwL8NIvATKuzES
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1Lb9QwEB5BkYAL5U1ogSBV4uQ2sR1vcmy3XbU8FkSp1FvkV6QVKFt1dw_0xE_gN_JLOuM82i0gEOSWjJ3Y43Hmc-L5BmADIX1mKpcwbqxnEtcgzPjUMpNJV-gKHXIIpH03VvtH8vVxdnwpir_hh-g_uNHMCO9rmuAnrtq6IA2lCGzamoX-XxXFdbghVZKTXe9-7AmkOFpnE18kBKM09B1tY8K3lusvu6WfsOYVt7SMZIMrGq2C7jrR7ED5vLmYm017doXf8X96eRfutDg13m4M6x5c8_V9uDXs0sM9gJ1DHBE_vUijEw-bXe_xpI4RVcbvz6a1__Ht--jU-_jwa43XZpNZPK2CZOL87CEcjfY-DfdZm5CBWUqSzjLncLWjB14VVuSm0py2cya51k5QA6vCcuuVJVSZudQXOSc44LLcWOW4Eo9gpcZnP4FYSWe1yLwYiFRqq4ymsFgsnzgvdWojYN14lLZlK6ekGV_KhmeZl6SZstdMBK_68icNT8dvS653w1u283VWpjkeGUK15NfigngjFa4dI3jZi1Hh9HdF1366CLeQckCIMoLHjdX0LSGKoVzkPIKNy2bUy0OIdCEQKQQMH0H6N8WGrV6IvWAeAQ929Ifel9vjg73-7Om_VHoBNz_sjsq3B-M3a3CbE8xJJONyHVbmpwv_DEHa3DwP8_AcIwIvyg
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Stereoelectronic+Control+in+the+Ozone-Free+Synthesis+of+Ozonides&rft.jtitle=Angewandte+Chemie+International+Edition&rft.au=dosPassosGomes%2C+Gabriel&rft.au=Yaremenko%2C+Ivan+A&rft.au=Radulov%2C+Peter+S&rft.au=Novikov%2C+Roman+A&rft.date=2017-04-24&rft.pub=Wiley+Subscription+Services%2C+Inc&rft.issn=1433-7851&rft.eissn=1521-3773&rft.volume=56&rft.issue=18&rft.spage=4955&rft_id=info:doi/10.1002%2Fanie.201610699&rft.externalDBID=NO_FULL_TEXT&rft.externalDocID=4321765307
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1433-7851&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1433-7851&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1433-7851&client=summon