Formation of new phosphates from aldehydes by a DBU-catalysed phospha-Brook rearrangement in a polar solvent

Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending on the solvent used. Apolar solvents give the normal Pudovik adduct, whereas the use of DBU in a polar solvent allows the formation of a phosp...

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Published inSynlett no. 15; pp. 2335 - 2336
Main Authors El Kaim, L, Gaultier, L, Grimaud, L, Dos Santos, A
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 19.09.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Pudovik reaction
phospha-Brook rearrangement
dialkylphosphite
ACID-ESTERS
phosphate esters
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Abstract Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending on the solvent used. Apolar solvents give the normal Pudovik adduct, whereas the use of DBU in a polar solvent allows the formation of a phosphate ester via phospha-Brook rearrangement of the intermediate hydroxyphosphonate.
AbstractList Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending on the solvent used. Apolar solvents give the normal Pudovik adduct, whereas the use of DBU in a polar solvent allows the formation of a phosphate ester via phospha-Brook rearrangement of the intermediate hydroxyphosphonate.
Author Grimaud, L
Dos Santos, A
El Kaim, L
Gaultier, L
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  fullname: Dos Santos, A
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Cites_doi 10.1021/cr960134o
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Issue 15
Keywords Pudovik reaction
phospha-Brook rearrangement
dialkylphosphite
ACID-ESTERS
phosphate esters
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References PATEL, DV (WOS:A1995TD46600022) 1995; 38
PUOVIK AN (WOS:000232045500018.11) 1969; 39
Rossi, RA (WOS:000180319600004) 2003; 103
KRUTIKOV, VI (WOS:A1986E237800019) 1986; 56
FLOYD AJ (WOS:000232045500018.2) 1970; 20
ABRUZOV BA (WOS:000232045500018.1) 1977; 9
PUDOVIK, AN (WOS:A1979GJ47100001) 1979
FOKIN AV (WOS:000232045500018.3) 1981; 7
PUDOVIK, AN (WOS:A1964WR08200022) 1964; 34
POLEZHAEVA NA (WOS:000232045500018.8) 1986; 8
KONOVALOVA IV (WOS:000232045500018.5) 1991; 61
Rowe, BJ (WOS:000170631200006) 2001; 12
TEXIERBOULLET, F (WOS:A1982PP33000003) 1982
TIMMLER, H (WOS:A1971L030300003) 1971; 104
GALLAGHER, MJ (WOS:A1969E818200064) 1969
References_xml – volume: 34
  start-page: 2902
  year: 1964
  ident: WOS:A1964WR08200022
  article-title: REAKTSII DIALKILTIOFOSFORISTYKH KISLOT S NEKOTORYMI KARBONILSODERZHASHCHIMI SOEDINENIYAMI
  publication-title: ZHURNAL OBSHCHEI KHIMII
  contributor:
    fullname: PUDOVIK, AN
– volume: 39
  start-page: 1018
  year: 1969
  ident: WOS:000232045500018.11
  publication-title: ZH OBSHCH KHIM
  contributor:
    fullname: PUOVIK AN
– start-page: 2605
  year: 1969
  ident: WOS:A1969E818200064
  article-title: ORGANOPHOSPHORUS INTERMEDIATES .2. REACTION OF TERVALENT PHOSPHORUS COMPOUNDS WITH TETRAPHENYLCYCLOPENTADIENONE
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC
  contributor:
    fullname: GALLAGHER, MJ
– volume: 8
  start-page: 1860
  year: 1986
  ident: WOS:000232045500018.8
  publication-title: IZV NAUK SSSR SER KH
  contributor:
    fullname: POLEZHAEVA NA
– volume: 103
  start-page: 71
  year: 2003
  ident: WOS:000180319600004
  article-title: Nucleophilic substitution reactions by electron transfer
  publication-title: CHEMICAL REVIEWS
  doi: 10.1021/cr960134o
  contributor:
    fullname: Rossi, RA
– volume: 104
  start-page: 3740
  year: 1971
  ident: WOS:A1971L030300003
  article-title: FORMATION OF PHOSPHORIC ACID ESTERS AND ALPHA-HYDROXYPHOSPHONIC ACID ESTERS BY TREATMENT OF DIALKYL PHOSPHITES WITH AROMATIC KETONES
  publication-title: CHEMISCHE BERICHTE-RECUEIL
  contributor:
    fullname: TIMMLER, H
– volume: 38
  start-page: 4557
  year: 1995
  ident: WOS:A1995TD46600022
  article-title: ALPHA-HYDROXY PHOSPHINYL-BASED INHIBITORS OF HUMAN RENIN
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: PATEL, DV
– volume: 20
  start-page: 1735
  year: 1970
  ident: WOS:000232045500018.2
  publication-title: TETRAHEDRON LETT
  contributor:
    fullname: FLOYD AJ
– start-page: 81
  year: 1979
  ident: WOS:A1979GJ47100001
  article-title: ADDITION-REACTIONS OF ESTERS OF PHOSPHORUS(III) ACIDS WITH UNSATURATED SYSTEMS
  publication-title: SYNTHESIS-STUTTGART
  contributor:
    fullname: PUDOVIK, AN
– volume: 61
  start-page: 1018
  year: 1991
  ident: WOS:000232045500018.5
  publication-title: ZH OBSHCH KHIM
  contributor:
    fullname: KONOVALOVA IV
– volume: 7
  start-page: 1655
  year: 1981
  ident: WOS:000232045500018.3
  publication-title: IZV AKAD NAUK SSSR S
  contributor:
    fullname: FOKIN AV
– volume: 9
  start-page: 2156
  year: 1977
  ident: WOS:000232045500018.1
  publication-title: IAN SSSR KH
  contributor:
    fullname: ABRUZOV BA
– volume: 12
  start-page: 1701
  year: 2001
  ident: WOS:000170631200006
  article-title: The synthesis of 1-hydroxy phosphonates of high enantiomeric excess using sequential asymmetric reactions: titanium alkoxide-catalyzed P-C bond formation and kinetic resolution
  publication-title: TETRAHEDRON-ASYMMETRY
  contributor:
    fullname: Rowe, BJ
– start-page: 916
  year: 1982
  ident: WOS:A1982PP33000003
  article-title: SYNTHESIS OF 1-HYDROXYALKANEPHOSPHONIC ESTERS ON ALUMINA
  publication-title: SYNTHESIS-STUTTGART
  contributor:
    fullname: TEXIERBOULLET, F
– volume: 56
  start-page: 2027
  year: 1986
  ident: WOS:A1986E237800019
  article-title: INTERACTION OF P(III) ACID-ESTERS WITH 1,5-DIHYDROPERFLUOROPENTANAL HYDRATE .6. ROLE OF SPECIFIC SOLVATION
  publication-title: ZHURNAL OBSHCHEI KHIMII
  contributor:
    fullname: KRUTIKOV, VI
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Snippet Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending...
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Chemistry, Organic
Physical Sciences
Science & Technology
Title Formation of new phosphates from aldehydes by a DBU-catalysed phospha-Brook rearrangement in a polar solvent
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