Reaction of N-(2,3-epoxypropyl)arenesulfonamides with (bicyclo[2.2.1]hept-5-en-endo-2-yl)methanamine

Abstract

Reactions of bicyclo[2.2.1]hept-5-en-endo-2-ylmethanamine with N-(2,3-epoxypropyl)arenesulfonamides gave amino alcohols having a norbornene fragment and sulfonamide group. The major products were formed via opening of the oxirane ring according to the Krasuskii rule. The product structure was determined by 1H and 13C NMR spectroscopy using DEPT and two-dimensional COSY, NOESY, HMQC, and HMBC techniques.