Chemoselective Protection of Aldehydes as Dithioacetals in Lithium Perchlorate-Diethyl Ether Medium. Evidence for the Formation of Oxocarbenium Ion Intermediate …

V Geetha Saraswathy…

Index: Saraswathy, V. Geetha; Sankararaman, S. Journal of Organic Chemistry, 1994 , vol. 59, # 16 p. 4665 - 4670

Full Text: HTML

Citation Number: 94

Abstract

Aldehydes and acetals were very efficiently converted to acyclic and cyclic dithioacetals in 5 M lithium perchlorate/diethyl ether (LPDE) medium at ambient temperature in high yields. Spectroscopic and other experimental evidences strongly suggest the formation of oxocarbenium ion intermediates from acetals in 5 M LPDE which subsequently reacted with thiols to give the dithioacetals. Under the same conditions ketones and their acetals also ...