Nucleophilic attacks on carbon-nitrogen double bonds. Part 4. Substitution of n-arylbenzimidoyl cyanides by amines in acetonitrile and by alkoxides in alcohols

Rachel Ta-Shma, Zvi Rappoport*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The substitution of the cyano-group of N-arylbenzimidoyl cyanides PhC(CN)=NC6H4Y by nucleophiles was studied. With amines in acetonitrile several reactions had showed first- (k′) and second-order (k″) terms in the amine. With EtO- in EtOH, both zero- (k0) and first-order (k′) terms in the nucieophile were found, while with Bu tO- in ButOH the reaction is of first order in the base. It is suggested that a common initial step in these reactions is nucleophilic attack of the amine, an alkoxide ion, or ethanol on the imidoyl cyanide. The subsequent expulsion of the leaving group may be uncatalysed or amine-catalysed in acetonitrile, and solvent-assisted in the alcohols. The reactions were compared with those of the corresponding N-arylbenzimidoyl chlorides.

Original languageEnglish
Pages (from-to)659-667
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number5
DOIs
StatePublished - 1977

Fingerprint

Dive into the research topics of 'Nucleophilic attacks on carbon-nitrogen double bonds. Part 4. Substitution of n-arylbenzimidoyl cyanides by amines in acetonitrile and by alkoxides in alcohols'. Together they form a unique fingerprint.

Cite this