Cycloaddition reactions across the carbon-carbon double bond of thiirene 1, 1-dioxide

M Komatsu, Y Yoshida, M Uesaka…

Index: Komatsu, Mitsuo; Yoshida, Yasuo; Uesaka, Masatoshi; Ohshiro, Yoshiki; Agawa, Toshio Journal of Organic Chemistry, 1984 , vol. 49, # 7 p. 1300 - 1302

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Citation Number: 12

Abstract

8a (34%) 8b (45%) 3-(p-nitrophenyl)-2, 5, 6-triphenyl-174-thiazine 1, l-dioxide (7a); the minor product was 2-(p-nitrophenyl)-3, 4, 5-tri-phenylpyrrole (Sa). The NMR spectrum of the thiazine 7a is featured by a broad singlet at 6 8.55 (one proton) which disappears upon addition of D20. 10 The formation of the thiazine 7a is explained by rearrangement of the 1: l cycloadduct 6a; elimination of sulfur dioxide from 6a would give rise to the pyrrole 8a. The ...