Generation of sulfur-functionalized nitrile oxide,(phenylthio)-acetonitrile oxide, and synthetic aplications.

S Kanemasa, Y Norisue, H Suga, O Tsuge

Index: Kanemasa, Shuji; Norisue, Yasumasa; Suga, Hiroyuki; Tsuge, Otohiko Bulletin of the Chemical Society of Japan, 1988 , vol. 61, # 11 p. 3973 - 3982

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Citation Number: 19

Abstract

The first generation of a new sulfur-functionalized nitrile oxide 1, 3-dipole,(phenylthio) acetonitrile oxide, is presented. Its cycloadditions to a variety of olefins and acetylenes lead to 3-(phenylthiomethyl)-2-isoxazolines and-oxazoles, the formers being selectively deprotonated at the carbon substituted by the sulfur moiety. The resulting sulfur-stabilized carbanions react with aldehydes, esteric Michael acceptors, and alkyl halides to enable ...