The stereochemical course of the generation and interception of a six-membered cyclic allene: 3 delta(2)-1H-naphthalene (2,3-didehydro-1,2-dihydronaphthalene)
The bromofluorocarbene adduct rac-1 of indene, possessing the fluorine atom at the endo position, is a useful substrate for the generation of the isonaphthalene 4 by the Doering-Moore-Skattebol reaction. By resolution of rac-1, an enantiomerically pure precursor of a six-membered cyclic allene was o...
Saved in:
Published in | European journal of organic chemistry Vol. 2006; no. 22; pp. 5045 - 5058 |
---|---|
Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
WEINHEIM
Wiley
13.11.2006
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | The bromofluorocarbene adduct rac-1 of indene, possessing the fluorine atom at the endo position, is a useful substrate for the generation of the isonaphthalene 4 by the Doering-Moore-Skattebol reaction. By resolution of rac-1, an enantiomerically pure precursor of a six-membered cyclic allene was obtained for the first time. The treatment of (+)- or (-)-1, dissolved in 2,5-dimethyl-, 2-tert-butyl-5-methyl-, or 2,5-bis(tert-butyl)furan, with methyllithium gave rise to the [4+2] cycloadducts 6 of 4 to the furans. It was shown by means of HPLC on Chiralcel OD that the formation of 6 proceeded with about 40 % ee, and that this value was independent of the type and concentration of the furan, and the reaction temperature. The absolute configurations of the enantiomers 1, aswell as those of the enantiomers 6, were determined by simulation of the CD spectra by quantum chemical methods and by the comparison of them with the experimental spectra. In the case of (+)-1, the reliability of this procedure was checked by X-ray crystal structure analysis. On the basis of these results, a model is proposed for the steric course of the reaction sequence, leading from a pure enantiomer 1 to the 70:30 mixtures of the product enantiomers 6. The use of indene as trapping reagent for 4 furnished the [2+2] cycload-duct 15. For the preparation of rac-15, the particularly simple one-pot procedure was employed, in which indene, tetrabromomethane, and methyllithium were combined and in which the dibromocarbene adduct 2 of indene serves as precursor of 4. Compound 2 could not be isolated, but was characterised by low-temperature H-1 NMR spectra. The conversion of (+)- or (-)-1 into 4 in the presence of indene afforded 15 only with a very low enantioselectivity. The constitutions and the relative configurations of 15 as well as the compounds 8 and 16, which resulted from thermolysis of the cycloadducts 6b and 15, respectively, were elucidated by X-ray crystal diffraction. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006). |
---|---|
AbstractList | The bromofluorocarbene adduct rac-1 of indene, possessing the fluorine atom at the endo position, is a useful substrate for the generation of the isonaphthalene 4 by the Doering-Moore-Skattebol reaction. By resolution of rac-1, an enantiomerically pure precursor of a six-membered cyclic allene was obtained for the first time. The treatment of (+)- or (-)-1, dissolved in 2,5-dimethyl-, 2-tert-butyl-5-methyl-, or 2,5-bis(tert-butyl)furan, with methyllithium gave rise to the [4+2] cycloadducts 6 of 4 to the furans. It was shown by means of HPLC on Chiralcel OD that the formation of 6 proceeded with about 40 % ee, and that this value was independent of the type and concentration of the furan, and the reaction temperature. The absolute configurations of the enantiomers 1, aswell as those of the enantiomers 6, were determined by simulation of the CD spectra by quantum chemical methods and by the comparison of them with the experimental spectra. In the case of (+)-1, the reliability of this procedure was checked by X-ray crystal structure analysis. On the basis of these results, a model is proposed for the steric course of the reaction sequence, leading from a pure enantiomer 1 to the 70:30 mixtures of the product enantiomers 6. The use of indene as trapping reagent for 4 furnished the [2+2] cycload-duct 15. For the preparation of rac-15, the particularly simple one-pot procedure was employed, in which indene, tetrabromomethane, and methyllithium were combined and in which the dibromocarbene adduct 2 of indene serves as precursor of 4. Compound 2 could not be isolated, but was characterised by low-temperature H-1 NMR spectra. The conversion of (+)- or (-)-1 into 4 in the presence of indene afforded 15 only with a very low enantioselectivity. The constitutions and the relative configurations of 15 as well as the compounds 8 and 16, which resulted from thermolysis of the cycloadducts 6b and 15, respectively, were elucidated by X-ray crystal diffraction. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006). |
Author | Arnone, Mario Deuerlein, Stephan Leusser, Dirk Braun, Martin Christl, Manfred Engels, Bernd Groetsch, Stefan Mueller, Germar Stalke, Dietmar Fischer, Hartmut |
Author_xml | – sequence: 1 givenname: Manfred surname: Christl fullname: Christl, Manfred email: christl@chemie.uni-wuerzburg.de – sequence: 2 givenname: Martin surname: Braun fullname: Braun, Martin – sequence: 3 givenname: Hartmut surname: Fischer fullname: Fischer, Hartmut – sequence: 4 givenname: Stefan surname: Groetsch fullname: Groetsch, Stefan – sequence: 5 givenname: Germar surname: Mueller fullname: Mueller, Germar – sequence: 6 givenname: Dirk surname: Leusser fullname: Leusser, Dirk – sequence: 7 givenname: Stephan surname: Deuerlein fullname: Deuerlein, Stephan – sequence: 8 givenname: Dietmar orcidid: 0000-0003-4392-5751 surname: Stalke fullname: Stalke, Dietmar email: dstalke@chemie.uni-goettingen.de – sequence: 9 givenname: Mario surname: Arnone fullname: Arnone, Mario – sequence: 10 givenname: Bernd surname: Engels fullname: Engels, Bernd email: engels@chemie.uni-wuerzburg.de |
BookMark | eNqVkL1OwzAUhS1UJFpgZfbYirpc21FEWCNQH6ADW-XaN8SVY0e2K8jL8KyYioERpvtzvnulcxZk5oNHQu44bDiAeMBj0BsBUANUlbwgcw5Nw6BuYFb6SlaMN_L1iixSOgJAU9d8Tj53PdKUMWLQPQ5WK0d1OMWENHQ0F_ENPUaVbfBUeUOtL7DG8bwoiKLJfrABh0P5YaietLOaKufK2ROV1KDLailWjG-ZV2Ofe_Ut0aVYS2aswX4yMTC-FmU697-o1Q257JRLePtTr8n9y_Ou3bJ3PIQuaYte436MdlBx2hdXohISoORRDMr_0o9_p1ubz5m04eSz_AKgJ3i5 |
Cites_doi | 10.1002/chem.200305000 10.1021/jp037010h 10.1021/ja011227c |
ContentType | Journal Article |
DBID | 1KM BLEPL DTL GAHYA |
DOI | 10.1002/ejoc.200600443 |
DatabaseName | Index Chemicus Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2006 |
DatabaseTitle | Web of Science |
DatabaseTitleList | Web of Science |
Database_xml | – sequence: 1 dbid: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Index Database Enrichment Source |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Chemistry |
EISSN | 1099-0690 |
EndPage | 5058 |
ExternalDocumentID | 000242300100009 |
GroupedDBID | -~X .3N .GA .Y3 05W 0R~ 10A 1KM 1L6 1OC 31~ 33P 3SF 3WU 4.4 4ZD 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 53G 5GY 5VS 66C 702 77Q 7PT 8-0 8-1 8-3 8-4 8-5 8UM 930 A03 AABCJ AAESR AAEVG AAHHS AANLZ AAONW AASGY AAXRX AAZKR ABCQN ABCUV ABEML ABIJN ABJNI ABLJU ABPVW ACAHQ ACBWZ ACCFJ ACCZN ACGFS ACIWK ACNCT ACPOU ACSCC ACXBN ACXQS ADBBV ADEOM ADIZJ ADKYN ADMGS ADOZA ADXAS ADZMN ADZOD AEEZP AEIGN AEIMD AENEX AEQDE AEUQT AEUYR AFBPY AFFNX AFFPM AFGKR AFPWT AFZJQ AHBTC AITYG AIURR AIWBW AJBDE AJXKR ALAGY ALMA_UNASSIGNED_HOLDINGS ALUQN AMBMR AMYDB ATUGU AUFTA AZBYB AZFZN AZVAB BAFTC BDRZF BFHJK BHBCM BLEPL BMNLL BMXJE BNHUX BROTX BRXPI BY8 CS3 D-E D-F DCZOG DPXWK DR2 DRFUL DRSTM DTL EBS EJD F00 F01 F04 F5P FEDTE G-S G.N GNP GODZA GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED H.T H.X HBH HGLYW HHY HHZ HVGLF HZ~ IX1 J0M JPC KQQ LATKE LAW LC2 LC3 LEEKS LH4 LITHE LOXES LP6 LP7 LUTES LW6 LYRES MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MVM MXFUL MXSTM N04 N05 N9A NF~ NNB O66 O9- OIG P2P P2W P2X P4D Q.N Q11 QB0 QRW R.K RNS ROL RWI RX1 SUPJJ TN5 UB1 UPT V2E W8V W99 WBFHL WBKPD WH7 WIH WIK WJL WOHZO WQJ WRC WXSBR WYISQ XG1 XJT XOL XPP XV2 ~IA ~WT |
ID | FETCH-webofscience_primary_0002423001000093 |
ISICitedReferencesCount | 28 |
ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000242300100009 |
ISSN | 1434-193X |
IngestDate | Wed Sep 18 06:09:03 EDT 2024 Fri Oct 04 21:02:44 EDT 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 22 |
Keywords | enantioselectivity APPROXIMATION CONVERSION cycloadditions quantum chemistry calculations COMPUTATIONAL ASSESSMENT ELECTRONIC-STRUCTURES ATOMS LI CYCLOALLENES 1,2,4-CYCLOHEXATRIENE cyclic allenes CD spectra CHIRALITY DERIVATIVES GAUSSIAN-BASIS SETS |
Language | English |
LinkModel | OpenURL |
LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
MergedId | FETCHMERGED-webofscience_primary_0002423001000093 |
ORCID | 0000-0003-4392-5751 |
PageCount | 14 |
ParticipantIDs | webofscience_primary_000242300100009 webofscience_primary_000242300100009CitationCount |
PublicationCentury | 2000 |
PublicationDate | 2006-11-13 |
PublicationDateYYYYMMDD | 2006-11-13 |
PublicationDate_xml | – month: 11 year: 2006 text: 2006-11-13 day: 13 |
PublicationDecade | 2000 |
PublicationPlace | WEINHEIM |
PublicationPlace_xml | – name: WEINHEIM |
PublicationTitle | European journal of organic chemistry |
PublicationTitleAbbrev | EUR J ORG CHEM |
PublicationYear | 2006 |
Publisher | Wiley |
Publisher_xml | – name: Wiley |
References | CHRISTL, M (WOS:A1989BR38M00009) 1989; 273 Christl, M (WOS:000072490300006) 1998; 1998 VOLCHOV NV (WOS:000242300100009.47) 1990 BECKE, AD (WOS:A1988Q146900044) 1988; 38 ELIEL EL (WOS:000242300100009.20) 1994 EMANUEL, CJ (WOS:A1994NV42100069) 1994; 116 CHRISTL, M (WOS:A1992JD99400029) 1992; 31 Nendel, M (WOS:000078548200048) 1999; 64 EICHKORN, K (WOS:A1995RT13600020) 1995; 242 Bauernschmitt, R (WOS:000073887300016) 1998; 120 DOLBIER, WR (WOS:A1992JX10900002) 1992; 48 JUNG, KY (WOS:A1989CB51400011) 1989; 54 SHELDRICK GM (WOS:000242300100009.41) 1997 MUNRO, DN (WOS:A1982PE51500017) 1982 KOTTKE, T (WOS:A1993LU53700018) 1993; 26 BRUK NON INC (WOS:000242300100009.2) 2000 Elliott, RL (WOS:A1997XN35700023) 1997; 62 MILLER, WT (WOS:A1959WB36900074) 1959; 81 CHRISTL M (WOS:000242300100009.13) 2004 Kottke, T (WOS:A1996VF65000022) 1996; 29 Christl, M (WOS:000089433600010) 2000; 39 Schoneboom, JC (WOS:000185933100008) 2003; 9 HANKINSON, B (WOS:A1972N851200030) 1972 SCHAFER, A (WOS:A1992JJ41100041) 1992; 97 Stalke, D (WOS:000074059200001) 1998; 27 Grimme, S (WOS:000228725900003) 2004; 20 Musch, PW (WOS:000187279000047) 2003; 107 BENSON SW (WOS:000242300100009.11) 1976 PARHAM, WE (WOS:A1956WB83000045) 1956; 78 SCHLOSSER, M (WOS:A1971J592100032) 1971; 104 VAHTRAS, O (WOS:A1993MB41700014) 1993; 213 SCHAFER, A (WOS:A1994NF08100043) 1994; 100 BRUK NON INC (WOS:000242300100009.1) 2000 LEE, CT (WOS:A1988L976200011) 1988; 37 Engels, B (WOS:000173218400024) 2002; 124 WOODWARD, RB (WOS:A1969E733100001) 1969; 8 AHLRICHS R (WOS:000242300100009.3) 2005 VOLCHKOV NV (WOS:000242300100009.48) 1989 ANGUS, RO (WOS:A1985ABE0400002) 1985; 107 SHELDRICK, GM (WOS:A1990DJ92700008) 1990; 46 BALCI, M (WOS:A1980KS95400057) 1980; 102 Groetsch, S (WOS:000087639800008) 2000; 56 FARRUGIA LJ (WOS:000242300100009.24) 1999; 32 SKATTEBOL, L (WOS:A1961WR19000002) 1961 EICHKORN, K (WOS:A1995RG42300007) 1995; 240 Bauernschmitt, R (WOS:A1996UX01700015) 1996; 256 BECKE, AD (WOS:A1993KV99700048) 1993; 98 SHELDRICK GM (WOS:000242300100009.42) 2002 BALCI, M (WOS:A1981LR07300070) 1981; 103 |
References_xml | – volume: 9 start-page: 4641 year: 2003 ident: WOS:000185933100008 article-title: Computational assessment of the electronic structure of 1-azacyclohexa-2,3,5-triene (3 delta(2)-1H-pyridine) and its benzo derivative (3 delta(2)-1H-quinoline) as well as generation and interception of 1-methyl-3 delta(2)-1H-quinoline publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200305000 contributor: fullname: Schoneboom, JC – volume: 39 start-page: 3261 year: 2000 ident: WOS:000089433600010 article-title: The dimerization of chiral allenes: Pairs of enantiomers and pairs of homomers furnish different diastereomers publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Christl, M – volume: 273 start-page: 121 year: 1989 ident: WOS:A1989BR38M00009 article-title: GENERATION AND INTERCEPTION OF 1-OXA-2,3-CYCLOHEXADIENE AND 1,2,4-CYCLOHEXATRIENE publication-title: STRAIN AND ITS IMPLICATIONS IN ORGANIC CHEMISTRY contributor: fullname: CHRISTL, M – volume: 103 start-page: 2874 year: 1981 ident: WOS:A1981LR07300070 article-title: TRAPPING AND CHIRALITY AS EVIDENCE FOR AN ALLENE STRUCTURE FOR 2,3,6-BICYCLO[3.2.1]OCTATRIENE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: BALCI, M – volume: 37 start-page: 785 year: 1988 ident: WOS:A1988L976200011 article-title: DEVELOPMENT OF THE COLLE-SALVETTI CORRELATION-ENERGY FORMULA INTO A FUNCTIONAL OF THE ELECTRON-DENSITY publication-title: PHYSICAL REVIEW B contributor: fullname: LEE, CT – volume: 1998 start-page: 237 year: 1998 ident: WOS:000072490300006 article-title: Cycloallenes, 12 - 3 delta(2)-chromene (2,3-didehydro-2H-1-benzopyran): Generation and interception publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Christl, M – volume: 54 start-page: 5667 year: 1989 ident: WOS:A1989CB51400011 article-title: SYNTHESIS OF 1,4-DIMETHYLPHENANTHRENES, 2,4-DIMETHYLPHENANTHRENES, AND 3,4-DIMETHYLPHENANTHRENE - A NOVEL DEOXYGENATION OF ARENE 1,4-ENDOXIDES WITH TRIMETHYLSILYL IODIDE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: JUNG, KY – start-page: 2372 year: 1972 ident: WOS:A1972N851200030 article-title: ARYNE CHEMISTRY .30. APPROACHES TO SYNTHESIS OF 9-ALKYL- AND 9,10-DIALKYL-1,2,3,4,5,6,7,8-OCTAFLUORO-9,10-DIHYDRO-9,10 ORTHO BENZENOANTHRACENES (9-ALKYL- AND 9,10-DIALKYL-1,2,3,4,5,6,7,8-OCTAFLUOROTRIPTYCENES) publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: HANKINSON, B – volume: 38 start-page: 3098 year: 1988 ident: WOS:A1988Q146900044 article-title: DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR publication-title: PHYSICAL REVIEW A contributor: fullname: BECKE, AD – volume: 98 start-page: 5648 year: 1993 ident: WOS:A1993KV99700048 article-title: DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE publication-title: JOURNAL OF CHEMICAL PHYSICS contributor: fullname: BECKE, AD – volume: 107 start-page: 11223 year: 2003 ident: WOS:000187279000047 article-title: Comprehensive model for the electronic structures of 1,2,4-cyclohexatriene and related compounds publication-title: JOURNAL OF PHYSICAL CHEMISTRY A doi: 10.1021/jp037010h contributor: fullname: Musch, PW – volume: 78 start-page: 1437 year: 1956 ident: WOS:A1956WB83000045 article-title: THE FORMATION OF NAPHTHALENES FROM INDENES .2. publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: PARHAM, WE – start-page: 243 year: 2004 ident: WOS:000242300100009.13 publication-title: MODERN ALLENE CHEM contributor: fullname: CHRISTL M – volume: 32 start-page: 837 year: 1999 ident: WOS:000242300100009.24 publication-title: J APPL CRYSTALLOGR contributor: fullname: FARRUGIA LJ – volume: 100 start-page: 5829 year: 1994 ident: WOS:A1994NF08100043 article-title: FULLY OPTIMIZED CONTRACTED GAUSSIAN-BASIS SETS OF TRIPLE ZETA VALENCE QUALITY FOR ATOMS LI TO KR publication-title: JOURNAL OF CHEMICAL PHYSICS contributor: fullname: SCHAFER, A – volume: 104 start-page: 1934 year: 1971 ident: WOS:A1971J592100032 article-title: FLUORO ORGANIC SYNTHESES .3. MONOFLUOROCARBENE publication-title: CHEMISCHE BERICHTE-RECUEIL contributor: fullname: SCHLOSSER, M – start-page: 309 year: 1976 ident: WOS:000242300100009.11 publication-title: THERMOCHEMICAL KINET contributor: fullname: BENSON SW – volume: 26 start-page: 615 year: 1993 ident: WOS:A1993LU53700018 article-title: CRYSTAL HANDLING AT LOW-TEMPERATURES publication-title: JOURNAL OF APPLIED CRYSTALLOGRAPHY contributor: fullname: KOTTKE, T – year: 1997 ident: WOS:000242300100009.41 publication-title: SHELXL 97 PROGRAM ST contributor: fullname: SHELDRICK GM – volume: 116 start-page: 5991 year: 1994 ident: WOS:A1994NV42100069 article-title: MECHANISM OF THE REACTION OF ATOMIC CARBON WITH PYRROLE - EVIDENCE FOR THE INTERMEDIACY OF A NOVEL DEHYDROPYRIDINIUM YLIDE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: EMANUEL, CJ – volume: 102 start-page: 7607 year: 1980 ident: WOS:A1980KS95400057 article-title: CHIRALITY AS A PROBE FOR THE STRUCTURE OF 1,2-CYCLOHEPTADIENE AND 1,2-CYCLOHEXADIENE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: BALCI, M – year: 2000 ident: WOS:000242300100009.1 publication-title: SAINT NT contributor: fullname: BRUK NON INC – volume: 107 start-page: 532 year: 1985 ident: WOS:A1985ABE0400002 article-title: SMALL-RING CYCLIC CUMULENES - THEORETICAL-STUDIES OF THE STRUCTURE AND BARRIER TO INVERSION IN CYCLIC ALLENES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: ANGUS, RO – start-page: CH13 year: 1994 ident: WOS:000242300100009.20 publication-title: STEREOCHEMISTRY ORGA contributor: fullname: ELIEL EL – volume: 242 start-page: 652 year: 1995 ident: WOS:A1995RT13600020 article-title: AUXILIARY BASIS-SETS TO APPROXIMATE COULOMB POTENTIALS (VOL 240, PG 283, 1995) publication-title: CHEMICAL PHYSICS LETTERS contributor: fullname: EICHKORN, K – start-page: 603 year: 1982 ident: WOS:A1982PE51500017 article-title: DIRECT CONVERSION OF FURAN INTO 2,5-DI-TERT-BUTYLFURAN publication-title: CHEMISTRY & INDUSTRY contributor: fullname: MUNRO, DN – start-page: 1935 year: 1989 ident: WOS:000242300100009.48 publication-title: IAN SSSR KH contributor: fullname: VOLCHKOV NV – volume: 29 start-page: 465 year: 1996 ident: WOS:A1996VF65000022 article-title: Low-cost conversion of a coaxial nozzle arrangement into a stationary low-temperature attachment publication-title: JOURNAL OF APPLIED CRYSTALLOGRAPHY contributor: fullname: Kottke, T – volume: 8 start-page: 781 year: 1969 ident: WOS:A1969E733100001 article-title: CONSERVATION OF ORBITAL SYMMETRY publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: WOODWARD, RB – volume: 31 start-page: 473 year: 1992 ident: WOS:A1992JD99400029 article-title: CYCLOALLENES .8. 1,2,4-CYCLOHEXATRIENE, AN ISOBENZENE, AND BICYCLO[4.4.0]DECA-1,3,5,7,8-PENTAENE, AN ISONAPHTHALENE - GENERATION AND TRAPPING REACTIONS publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: CHRISTL, M – start-page: 1609 year: 1990 ident: WOS:000242300100009.47 publication-title: IZV AKAD NAUK SSSR contributor: fullname: VOLCHOV NV – volume: 213 start-page: 514 year: 1993 ident: WOS:A1993MB41700014 article-title: INTEGRAL APPROXIMATIONS FOR LCAO-SCF CALCULATIONS publication-title: CHEMICAL PHYSICS LETTERS contributor: fullname: VAHTRAS, O – volume: 62 start-page: 4998 year: 1997 ident: WOS:A1997XN35700023 article-title: Cycloadditions of cephalosporins. A comprehensive study of the reaction of cephalosporin triflates with olefins, acetylenes, and dienes to form [2+2] and [4+2] adducts publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Elliott, RL – volume: 124 start-page: 287 year: 2002 ident: WOS:000173218400024 article-title: Cycloallenes. Part 17 . Computational assessment of the electronic structures of cyclohexa-1,2,4-triene, 1-oxacyclohexa-2,3,5-triene (3 delta(2)-pyran), their benzo derivatives, and cyclohexa-1,2-diene. An experimental approach to 3 delta(2)-pyran publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja011227c contributor: fullname: Engels, B – volume: 256 start-page: 454 year: 1996 ident: WOS:A1996UX01700015 article-title: Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory publication-title: CHEMICAL PHYSICS LETTERS contributor: fullname: Bauernschmitt, R – volume: 97 start-page: 2571 year: 1992 ident: WOS:A1992JJ41100041 article-title: FULLY OPTIMIZED CONTRACTED GAUSSIAN-BASIS SETS FOR ATOMS LI TO KR publication-title: JOURNAL OF CHEMICAL PHYSICS contributor: fullname: SCHAFER, A – volume: 120 start-page: 5052 year: 1998 ident: WOS:000073887300016 article-title: Experiment versus time dependent density functional theory prediction of fullerene electronic absorption publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Bauernschmitt, R – volume: 81 start-page: 5008 year: 1959 ident: WOS:A1959WB36900074 article-title: REACTIONS OF ALKYLLITHIUMS WITH POLYHALIDES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MILLER, WT – year: 2000 ident: WOS:000242300100009.2 publication-title: GEMINI 1 02 contributor: fullname: BRUK NON INC – year: 2002 ident: WOS:000242300100009.42 publication-title: SADABS 2 10 PROGRAM contributor: fullname: SHELDRICK GM – volume: 48 start-page: 9649 year: 1992 ident: WOS:A1992JX10900002 article-title: THE THERMAL-CONVERSIONS OF 6,6-DIFLUOROBICYCLO[3.1.0]HEX-2-ENES TO FLUOROBENZENES - AN INTERESTING DICHOTOMY OF MECHANISMS publication-title: TETRAHEDRON contributor: fullname: DOLBIER, WR – volume: 20 start-page: 153 year: 2004 ident: WOS:000228725900003 article-title: Calculation of the electronic spectra of large molecules publication-title: REVIEWS IN COMPUTATIONAL CHEMISTRY, VOL 20 contributor: fullname: Grimme, S – volume: 56 start-page: 4163 year: 2000 ident: WOS:000087639800008 article-title: Cycloallenes. Part 15: 3 delta(2)-1H-naphthalene (2,3-didehydro-1,2-dihydronaphthalene) from 3-bromo-1,2-dihydronaphthalene publication-title: TETRAHEDRON contributor: fullname: Groetsch, S – volume: 240 start-page: 283 year: 1995 ident: WOS:A1995RG42300007 article-title: AUXILIARY BASIS-SETS TO APPROXIMATE COULOMB POTENTIALS publication-title: CHEMICAL PHYSICS LETTERS contributor: fullname: EICHKORN, K – volume: 64 start-page: 976 year: 1999 ident: WOS:000078548200048 article-title: Strained allenes as dienophiles in the Diels-Alder reaction: An experimental and computational study publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Nendel, M – volume: 27 start-page: 171 year: 1998 ident: WOS:000074059200001 article-title: Cryo crystal structure determination and application to intermediates publication-title: CHEMICAL SOCIETY REVIEWS contributor: fullname: Stalke, D – volume: 46 start-page: 467 year: 1990 ident: WOS:A1990DJ92700008 article-title: PHASE ANNEALING IN SHELX-90 - DIRECT METHODS FOR LARGER STRUCTURES publication-title: ACTA CRYSTALLOGRAPHICA SECTION A contributor: fullname: SHELDRICK, GM – year: 2005 ident: WOS:000242300100009.3 publication-title: TURBOMOLE V5 8 contributor: fullname: AHLRICHS R – start-page: 167 year: 1961 ident: WOS:A1961WR19000002 article-title: ALLENES FROM GEM-DIHALOCYCLOPROPANE DERIVATIVES AND ALKYLLITHIUM publication-title: TETRAHEDRON LETTERS contributor: fullname: SKATTEBOL, L |
SSID | ssj0009661 |
Score | 4.035393 |
Snippet | The bromofluorocarbene adduct rac-1 of indene, possessing the fluorine atom at the endo position, is a useful substrate for the generation of the... |
Source | Web of Science |
SourceID | webofscience |
SourceType | Index Database Enrichment Source |
StartPage | 5045 |
SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
Title | The stereochemical course of the generation and interception of a six-membered cyclic allene: 3 delta(2)-1H-naphthalene (2,3-didehydro-1,2-dihydronaphthalene) |
URI | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000242300100009 |
Volume | 2006 |
WOS | 000242300100009 |
WOSCitedRecordID | wos000242300100009 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1NT9wwELVW9EAvVQutCrTIB5BAi9usnQ0JN5R-rCq1h5ZKe0OJ43Sp2AQtWan0x_RvcmXGE2-yqxy2XKLEsRwl8zIztmfeMHaQJNKEuZEggWEm_ATmrFEwCIRJQx2CvfN1iju6X78Fo5_-l_Fw3Ovdt6KW5lX6Tv_tzCt5jFShDeSKWbL_IdnFoNAA5yBfOIKE4bi2jJHowGDZq2nN9YFRGW7n_5clla5cyDFyQ7g4FkqMvL36I6YGi4KA46nvNFJe2-oqNmVd9TNzje5lKA9lJAYjUSQ3k2qSYIc-NcdKZFeZmdxls1KAWowlXNurVl-33tC1BVC7w1ReSve1q0DXBB6gHrqmxKIid6VFKQ5gXtQJR45BPLHV3B0SR3BjOl9E9nyelaa6peJXPyqT139Gs-iBgXdqWbW2tLavfAGe6JiMGrV5ll6BapE6VY9DtUBNGdG16h56xGtZuwHgGYadJoYoa83v0hJgBrgjrhpj6gIIVmzsIvLRs06Rwqm4ZxNPn8jTaIirBh--N7xnMAe1KwXuvRzbqCffLz-4012yrtHFc_asntPwcwLoC9YzxRbbjJ0gt9k_ACpfBionoPIy5wBU3gCVA1B5G6jYJeFtoHICKiegnnHFLUyP5PEKRPmRPFmC50kXOI9fsv6njxfxSLRf8vKGeFguV76lesU2irIwrxkPM-WlyWmugyzzwyAKDdjRKA3yII-krwc77GCdEXfYYJ1ucc2mjywS1e56Q--xpw2u37CNajY3b8G9rdJ9C4UH-pOqzA |
link.rule.ids | 315,786,790,27957,27958 |
linkProvider | Wiley-Blackwell |
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=The+stereochemical+course+of+the+generation+and+interception+of+a+six-membered+cyclic+allene%3A+3+delta%282%29-1H-naphthalene+%282%2C3-didehydro-1%2C2-dihydronaphthalene%29&rft.jtitle=European+journal+of+organic+chemistry&rft.au=Christl%2C+Manfred&rft.au=Braun%2C+Martin&rft.au=Fischer%2C+Hartmut&rft.au=Groetsch%2C+Stefan&rft.date=2006-11-13&rft.pub=Wiley&rft.issn=1434-193X&rft.eissn=1099-0690&rft.volume=2006&rft.issue=22&rft.spage=5045&rft.epage=5058&rft_id=info:doi/10.1002%2Fejoc.200600443&rft.externalDBID=n%2Fa&rft.externalDocID=000242300100009 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1434-193X&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1434-193X&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1434-193X&client=summon |