A novel addition–rearrangement of O-(1-benzotriazolylalkyl)oximes with organolithium reagents. Convenient non-oxidative conversions of aldehydes into amides

Abstract

Condensation of an aldehyde, an oxime and benzotriazole gives an O-(1-benzotriazolylalkyl)oxime which undergoes an addition–rearrangement on treatment with an organolithium reagent. This reaction provides a novel non-oxidative method for the transformation of aldehydes into amides which has afforded several new N-monosubstituted amides with crowded structures. Grignard reactions of the O-(1-benzotriazolylalkyl)oximes give alcohols as the major products.