Oxidation of 2, 2, 3, 3-Tetramethyl-1, 4-diphenyl-5, 6-dithiabicyclo (2.1. 1)-hexane and Its Oxidation Products: An Important Role of 1, 3-Transannular Interaction in the …
…, MX Ding, K Maeda, J Nakayama, M Hoshino
Index: Ishii, Akihiko; Ding, Meng-Xin; Maeda, Kiyoto; Nakayama, Juzo; Hoshino, Masamatsu Bulletin of the Chemical Society of Japan, 1992 , vol. 65, # 12 p. 3343 - 3349
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Citation Number: 10
Abstract
Oxidation of 2, 2, 3, 3-tetramethyl-1, 4-diphenyl-5, 6-dithiabicyclo [2.1. 1] hexane with m- chloroperbenzoic acid gives two isomeric endo-(4a) and exo-sulfoxides (4b), three S, S′- dioxides (endo, exo-5a, exo, exo-5b, and endo, endo-5c), and an S, S, S′-trioxide (6). The relative reactivity to further oxidation is 4b>> 4a and 5b> 5a, which suggests that the attractive 1, 3-transannular interaction operative in 1, 3-dithietane part of 4a and 5a ...
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