Condensation‐ring Expansion Reaction of Formyl[2.2.1]bicyclic Carbinols with Para‐substituted Phenyl Amines: Application to the Preparation of [3.2.1]bicyclic N‐aryl‐1,2,3‐oxathiazolidine‐2‐oxide Agents

Abstract

AbstractIndividual reaction of camphene‐derived endo‐formyl[2.2.1]bicyclic carbinol and that of camphor‐derived exo‐formyl[2.2.1]bicyclic carbinol with parent and para‐substituted phenyl amines gave regio‐ and stereospecific corresponding [3.2.1]bicyclic (para‐substituted) phenyl amino ketones. Mechanism of each reaction was discussed. Some camphor‐derived [3.2.1]bicyclic amino ketones were reduced to [3.2.1]bicyclic (para‐substituted) phenyl amino alcohols, which were then treated with mesyl chloride to provide [3.2.1]bicyclic N‐phenyl/aryl‐1,2,3‐oxathiazolidine‐2‐oxide agents. The mechanism of this final reaction was discussed as well.