Intramolecular cycloaddition reactions of N-sulfonyl nitrile imides bearing alkenyl groups.

…, Y Hayashi, Y Nagano, K Teramura

Index: Shimizu, Tomio; Hayashi, Yoshiyuki; Nagano, Yoshio; Teramura, Kazuhiro Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 2 p. 429 - 434

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Citation Number: 20

Abstract

The reaction of the p-tolyl (or phenyl) sulfonylhydrazones of some 2-(alkenyloxy) benzaldehydes with lead tetraacetate leads, via the nitrile imide intermediates, Ar–\ overset+ C= N–\ overset− N–SO 2–C 6 H 4–Xp, to intramolecular 1, 3-dipolar cycloadducts and 1- acetyl-2-aroyl-1-p-tolyl (or phenyl) sulfonyl hydrazines in 20–65% and 7–70% yields respectively, while the intermolecular reactions of the benzaldehyde p- ...