Novel syntheses of 3-methylene-azetidin-2-one derivatives and related systems

…, AGM Barrett, P Quayle, A Walker, MJ Betts

Index: Adlington, Robert M.; Barrett, Anthony G. M.; Quayle, Peter; Walker, Andrew; Betts, Michael J. Journal of the Chemical Society, Chemical Communications, 1981 , # 9 p. 404 - 405

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Citation Number: 20

Abstract

Summary Syntheses of the title compounds via l-lithio- oxy- l-lithio-amino-allene derivatives or lithium phenyl- ethynolate are described. ... Reaction of the acrylamides (3) with 2 equiv. of n-butyl- lithium followed by toluene-4-sulphonyl chloride (TsC1) in tetrahydrofuran (THF) or 1,2-dimethoxyethane (DME) gave the p-lactams (5), (6), and (7) in good yields (Table and Scheme 1). The intermediate toluene-4-sulphonates (4) were isolated in some cases after brief ...