The Journal of Organic Chemistry

Formation of fused tricyclic azetidinones and pyrrolidinones by intramolecular SH2 processes

ALJ Beckwith, DR Boate

Index: Beckwith, A. L. J.; Boate, D. R. Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4339 - 4348

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Citation Number: 43

Abstract

Treatment of a variety of suitably substituted sulfides of N-(o-halobenzy1)-or N-(0- halopheny1) azetidinone (eg, 4 and 8) and-pyrrolidinone (eg, 12 and 14) systems with either tributylstannane or tributyltin deuteride affords, by aryl radical substitution at the sulfur atom, the corresponding tricyclic azetidinones (21 and 26) and pyrrolidinones (38 and 47). The reactions with tributyltin deuteride give, in addition to the cyclized product, products arising ...