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Volumn , Issue 9, 2008, Pages 1317-1320

A mild synthesis of nitriles by von Braun degradation of amides using triphenyl phosphite-halogen-based reagents

Author keywords

Amide degradation; Halotriphenoxyphosphonium halides; Imidoyl halides; Nitriles; Triphenyl phosphite

Indexed keywords

AMIDE; BROMINE DERIVATIVE; BROMOTRIPHENOXYPHOSPHONIUM BROMIDE; CHLORIDE; CHLOROFORM; CHLOROTRIPHENOXYPHOSPHONIUM CHLORIDE; HALOGEN; NITRILE; PHOSPHITE; REAGENT;

EID: 45749107612     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1072591     Document Type: Article
Times cited : (13)

References (33)
  • 3
    • 45749156323 scopus 로고
    • 2nd ed, Wasserman, H. H, Blomquist, A. T, Eds, Academic Press: San Diego, Chapt. 17, 549-584
    • (b) Sandler, S. R.; Karo, W. Organic Functional Group Preparations In Organic Chemistry, 2nd ed., Vol. 12-1; Wasserman, H. H.; Blomquist, A. T., Eds.; Academic Press: San Diego, 1983, Chapt. 17, 549-584.
    • (1983) Organic Functional Group Preparations In Organic Chemistry , vol.12 -1
    • Sandler, S.R.1    Karo, W.2
  • 5
    • 0004088819 scopus 로고
    • Rappoport, Z, Ed, Wiley-Interscience: New York
    • (a) The Chemistry of the Cyano Group; Rappoport, Z., Ed.; Wiley-Interscience: New York, 1970.
    • (1970) The Chemistry of the Cyano Group
  • 27
    • 45749118670 scopus 로고    scopus 로고
    • 13C NMR and elemental analysis were also performed.
    • 13C NMR and elemental analysis were also performed.
  • 29
    • 45749094505 scopus 로고    scopus 로고
    • 3N was not used). After leaving to warm to r.t. over a period of 3-4 h, the reaction mixture was gently heated to reflux for 16 h, except when TLC analysis already showed complete disappearance of the starting amide (see Table 1). The solvent was then evaporated under reduced pressure and the resulting nitrile was purified by column chromatography on silica gel.
    • 3N was not used). After leaving to warm to r.t. over a period of 3-4 h, the reaction mixture was gently heated to reflux for 16 h, except when TLC analysis already showed complete disappearance of the starting amide (see Table 1). The solvent was then evaporated under reduced pressure and the resulting nitrile was purified by column chromatography on silica gel.
  • 30
    • 45749139104 scopus 로고    scopus 로고
    • 9a,12
    • 9a,12
  • 31
    • 45749125974 scopus 로고    scopus 로고
    • D +111.5.
    • D +111.5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.