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The reaction of certain heterocyclic azides with triphenylphosphine
Author(s) -
Vanallan J. A.,
Reynolds G. A.
Publication year - 1968
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570050406
Subject(s) - chemistry , adduct , triphenylphosphine , nitrogen atom , phosphine , alkylation , nitrogen , organic chemistry , medicinal chemistry , methylation , ring (chemistry) , catalysis , dna , biochemistry
Azidobenzothiazole and azidobenzimidazole and certain of its derivatives react with triphenyl‐phosphine to give isolatable adducts which decompose thermally to give the corresponding phosphinimines. 2‐Azidobenzoxazole gives an adduct which loses nitrogen at 15–20° and gives the phosphinimine directly. Methylation of the phosphinimines occurs at the hetero nitrogen, whereas benzoylation occurs at the exo nitrogen atom. The structures of the alkylation and aroylation products of the phosphinimines were established.