Ramberg-Backlund reaction of 1, 3-dibromo-1H, 3H-naphtho [1, 8-cd] thiopyran 2, 2-dioxide. Formation of acenaphthyne intermediate

J Nakayama, E Ohshima, A Ishii…

Index: Nakayama, Juzo; Ohshima, Etsuo; Ishii, Akihiko; Hoshino, Masamatsu Journal of Organic Chemistry, 1983 , vol. 48, # 1 p. 60 - 65

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Citation Number: 14

Abstract

Radical bromination of lH, 3H-naphtho [l, 8-cd] thiopyran 2, 2-dioxide (15) gave the corresponding monobromo sulfone 16 (48%), dibromo sulfone 12 (43%; cis/trans= 64/36), and tribromo sulfone 17 (5%). Ramberg-Backlund reaction of 12 was investigated under a variety of conditions with expectation of the formation of thiirene dioxide 11 from which generation of acenaphthyne (5) would be expected both thermally and photochemically. ...