Abstract
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.
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