Adamantane chemistry. Part I. Some intramolecular ring expansion reactions of adamantan-2-one; the synthesis of 4-substituted homoadamantanes

Abstract

Conditions for the preparation of 4-substituted homoadamantanes, in good yield, by intramolecular ring expansion reactions of adamantan-2-one are described. The anomalous Beckmann and Schmidt rearrangements in this system have been studied, and a simple synthesis of endo-7-cyanobicyclo[3,3,1]non-2-ene is reported.