Tetrahedron

Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene: a concise synthesis of vinyl sulfide and nitro sulfide

…, P Wu, CC Wang, JT Liu, CW Kuo, YH Shin, CF Yao

Index: Chu, Cheng-Ming; Tu, Zhijay; Wu, Pohsi; Wang, Chieh-Chieh; Liu, Ju-Tsung; Kuo, Chun-Wei; Shin, Yu-Hsuan; Yao, Ching-Fa Tetrahedron, 2009 , vol. 65, # 19 p. 3878 - 3885

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Citation Number: 15

Abstract

Under catalyst-free reaction conditions, solvent-mediated addition of thiol 2 to β-nitrostyrene 1 proceeded with regioselective control to afford either adduct 3 or vinyl sulfide 4 in good to excellent yield. Thermodynamic and autocatalytic reaction mechanisms were proposed to rationalize the products thus formed.

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