Site selectivity in the reactions of various 1, 3-dipoles with (phenylsulfonyl)-1, 2-propadiene

A Padwa, SP Craig, U Chiacchio…

Index: Padwa, Albert; Craig, Stewart P.; Chiacchio, Ugo; Kline, Donald N. Journal of Organic Chemistry, 1988 , vol. 53, # 10 p. 2232 - 2238

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Citation Number: 27

Abstract

The cycloaddition reactions of (phenyhulfonyl)-l, 2-propadiene (1) with various l, &dipolea have been investigated. MNDO calculations suggest that the reaction of the activated allene will proceed in a highly regioselective fashion and undergo cycloaddition across the more activated a-bond. This proved to be the case in the reactions of diazomethane and diazopropane with 1. The formation of 44 (phenylsulfonyl) methyl] pyrazole (8) was ...