Azomethine derivatives. Part IV. The action of some organozinc compounds on diphenylketimine, phenyl cyanide, and t-butyl cyanide

Abstract

Diphenylketimine reacts at 30–65° with dimethyl-, diethyl-, and diphenyl-zinc to form the dimeric azomethine derivatives (Ph₂C:N·ZnR)₂. All are air- and moisture-sensitive thermally unstable solids. The phenyl compound disproportionates at 80° to give (Ph₂C:N)₂Zn, which can also be obtained by thermal decomposition of the nitrile adduct PhCN,ZnPh₂. Pyridine cleaves the (ZnN)₂ ring of (Ph₂C:N·ZnMe)₂ to form Ph₂C:N·ZnMe,2py. Diethylzinc catalyses the trimerisation of phenyl cyanide. No evidence of interaction was observed in studies of the systems R₂Zn–Bu^tCN (R = Me, Et, or Ph). Features of the infrared and proton magnetic resonance spectra of the azomethine derivatives are discussed.