Lewis acid-induced nucleophilic substitution reaction of. beta.-nitro sulfides

A Kamimura, H Sasatani, T Hashimoto…

Index: Kamimura, Akio; Sasatani, Hiroyuki; Hashimoto, Toshihiro; Ono, Noboru Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 4998 - 5003

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Citation Number: 23

Abstract

The nitro group of@-nitro sulfides is readily substituted by an allyl or a cyano group or hydrogen on treatment with allyltrimethylsilane, cyanotrimethylsilane, or triethylsilane in the presence of an appropriate Lewis acid. The intramolecular Friedelxrafts reaction of@-nitro sulfides is also induced by a Lewis acid. Primary and secondary nitro groups as well as tertiary and benzylic nitro groups undergo this substitution reaction. These replacements ...