An approach toward azacycles using photochemical and radical cyclizations of N-alkenyl substituted 5-thioxopyrrolidin-2-ones

A Padwa, MN Jacquez, A Schmidt

Index: Padwa, Albert; Jacquez, Martin N.; Schmidt, Andreas Journal of Organic Chemistry, 2004 , vol. 69, # 1 p. 33 - 45

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Citation Number: 9

Abstract

The photochemical reactions of a series of cyclic N-alkenyl-substituted thioimides have been examined. Irradiation of N-3-methylbut-3-enyl-5-thioxo-pyrrolidin-2-one (16) results in intramolecular [2+ 2] cycloaddition to give the highly strained thietane 17, whose structure was confirmed on the basis of its X-ray analysis. Treatment of cycloadduct 17 with dimethyl (methylthio) sulfonium tetrafluoroborate gave 2, 5, 6, 7-tetrahydropyrrolizin-3-one (20) in ...