New versatile approach to alpha-hydrazonoesters and amino acid derivatives through a modified Japp-Klingemann reaction

Addition of diazonium tetrafluoroborates to an acyl chloride pyridine mixture affords hydrazonoacid derivatives in smooth conditions; this new Japp-Klingemann reaction emphasizes the synthetic potential of electrophilic addition to ketenes.

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Published inChemical communications (Cambridge, England) no. 15; pp. 1385 - 1386
Main Authors Atlan, El Kaim, L, Supiot, C
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2000
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
SALTS
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Abstract Addition of diazonium tetrafluoroborates to an acyl chloride pyridine mixture affords hydrazonoacid derivatives in smooth conditions; this new Japp-Klingemann reaction emphasizes the synthetic potential of electrophilic addition to ketenes.
AbstractList Addition of diazonium tetrafluoroborates to an acyl chloride pyridine mixture affords hydrazonoacid derivatives in smooth conditions; this new Japp-Klingemann reaction emphasizes the synthetic potential of electrophilic addition to ketenes.
Author Atlan
El Kaim, L
Supiot, C
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References HUTCHINS RO (WOS:000088225700019.9) 1991; 8
BARTLETT, PD (WOS:A19633099B00003) 1963; 85
HARADA K (WOS:000088225700019.8) 1991; 8
BOIVIN, J (WOS:A1995QK68100011) 1995; 51
ESCHENMOSER, A (WOS:A19679035600031) 1967; 50
SAKAKURA, T (WOS:A1994MV45700012) 1994
BOWADT S (WOS:000088225700019.4) 1989
PHILLIPS RR (WOS:000088225700019.10) 1959; 10
COREY, EJ (WOS:A1970G015100045) 1970; 92
BURK, MJ (WOS:A1994PX86000014) 1994; 35
VIEHE, HG (WOS:A1977DD13000017) 1977; 16
SAKAKURA T (WOS:000088225700019.12) 1985
ADLINGTON, RM (WOS:A1983QE51800006) 1983; 16
References_xml – volume: 16
  start-page: 55
  year: 1983
  ident: WOS:A1983QE51800006
  article-title: RECENT APPLICATIONS OF THE SHAPIRO REACTION
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  contributor:
    fullname: ADLINGTON, RM
– start-page: 1309
  year: 1985
  ident: WOS:000088225700019.12
  publication-title: CHEM COMMUN
  contributor:
    fullname: SAKAKURA T
– volume: 85
  start-page: 1864
  year: 1963
  ident: WOS:A19633099B00003
  article-title: PERESTERS .11. DI-TERT-BUTYLPEROXY DIPHENYLMALONATE - ALPHA-LACTONE INTERMEDIATES IN FREE RADICAL REACTIONS
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: BARTLETT, PD
– volume: 8
  start-page: 139
  year: 1991
  ident: WOS:000088225700019.8
  publication-title: COMPREHENSIVE ORGANI
  contributor:
    fullname: HARADA K
– volume: 8
  start-page: 327
  year: 1991
  ident: WOS:000088225700019.9
  publication-title: COMPREHENSIVE ORGANI
  contributor:
    fullname: HUTCHINS RO
– volume: 51
  start-page: 2573
  year: 1995
  ident: WOS:A1995QK68100011
  article-title: A NEW AND EFFICIENT SYNTHESIS OF TRIFLUOROMETHYL KETONES FROM CARBOXYLIC-ACIDS .1.
  publication-title: TETRAHEDRON
  contributor:
    fullname: BOIVIN, J
– volume: 35
  start-page: 9363
  year: 1994
  ident: WOS:A1994PX86000014
  article-title: NEW CHIRAL 1,1'-BIS(PHOSPHOLANO)FERROCENE LIGANDS FOR ASYMMETRIC CATALYSIS
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: BURK, MJ
– volume: 92
  start-page: 2476
  year: 1970
  ident: WOS:A1970G015100045
  article-title: STUDIES ON ASYMMETRIC SYNTHESIS OF ALPHA-AMINO ACIDS .1. A NEW APPROACH
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: COREY, EJ
– volume: 50
  start-page: 708
  year: 1967
  ident: WOS:A19679035600031
  article-title: EINE NEUARTIGE FRAGMENTIERUNG CYCLISCHER ALPHA BETA-UNGESATTIGTER CARBONYLSYSTEME - SYNTHESE VON EXALTON UND RAC-MUSCON AUS CYCLODODECANON
  publication-title: HELVETICA CHIMICA ACTA
  contributor:
    fullname: ESCHENMOSER, A
– volume: 10
  start-page: 144
  year: 1959
  ident: WOS:000088225700019.10
  publication-title: ORGANIC REACTION
  contributor:
    fullname: PHILLIPS RR
– start-page: 289
  year: 1994
  ident: WOS:A1994MV45700012
  article-title: REACTION OF SILYL ENOL ETHERS WITH ARENEDIAZONIUM SALTS .2. ALPHA-AMINATION OF ESTERS
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
  contributor:
    fullname: SAKAKURA, T
– volume: 16
  start-page: 182
  year: 1977
  ident: WOS:A1977DD13000017
  article-title: REACTIONS OF ACYL CHLORIDES TRIETHYLAMINE OR KETENES WITH PHOSGENIMINIUM SALTS
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH
  contributor:
    fullname: VIEHE, HG
– start-page: 114
  year: 1989
  ident: WOS:000088225700019.4
  publication-title: SYNTHESIS-STUTTGART
  contributor:
    fullname: BOWADT S
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Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Title New versatile approach to alpha-hydrazonoesters and amino acid derivatives through a modified Japp-Klingemann reaction
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