Chemistry Letters, Vol.46, No.7, 960-963, 2017
Neighboring Group Participation of Thiofenchone with Acyl Chlorides: Novel Formation of 2-Acyloxy-2,7,7-trimethylnorbornan-1-thiols
Reaction of thiofenchone with acyl chlorides in the presence of AlCl3 in refluxing dichloromethane gave Wagner-Meerwein products and 2-acyloxynorbornan-1-thiols. When ZnCl2 was used as a Lewis acid, norbornan-1-thiols were obtained as major products along with Wagner-Meerwein products. The reaction might proceed through 5-membered cyclic carbocation (oxathiacarbocation) intermediates.