A one-pot, two step synthesis of 2, 2-disubstituted 1-nitroalkenes

YJ Jang, WW Lin, YK Shih, JT Liu, MH Hwang, CF Yao

Index: Jang, Yeong-Jiunn; Lin, Wen-Wei; Shih, Yuh-Kuo; Liu, Ju-Tsung; Hwang, Ming-Hsing; Yao, Ching-Fa Tetrahedron, 2003 , vol. 59, # 27 p. 4979 - 4992

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Citation Number: 16

Abstract

The reactions of ketones 1a–o, nitromethane 2, and a stoichiometric amount of piperidine 3a or ethylenediamine 3b in the presence of mercaptan 6a in THF or CH3CN solution give high yields of β-nitrosulfides 7a–o. The latter can be oxidized by 8a (m-CPBA or m-CPBA/AcOH) at 0° C, 8b (H2O2/AcOH), or 8c (H2O2) at room temperature, thus generating β- nitroalkylsulfoxides 9a–o, which then undergo elimination to produce medium to high ...