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]]Individual 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.[[note]]SC