Synthesis of Novel Heterocycles from Benzoin-α-oxime by Reaction with Electrophile­s

Abstract

A useful sequence of reactions for the synthesis of a variety of heterocyclic systems is described. The reaction of benzoin-α-oxime (2-hydroxy-1,2-diphenyl-1-ethanone oxime) with sodium hydride in propan-2-ol produces a 1,5-dianion. The cyclization of this dianion with dielectrophiles affords dioxazines, dioxazepines, dioxazocine, dioxazonine and dioxazaphosphines in good yields.

Key words

electrophilic cyclizations - benzoin-α-oxime - dioxazines - dioxazepines - dioxazocine - dioxazonine - dioxazaphosphines

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