Remote Pummerer Reaction via Intermolecular Through-Space Interaction between Sulfonium and Sulfenyl Sulfur Atoms

K Kobayashi, E Koyama, K Namatame…

Index: Kobayashi, Kenji; Koyama, Emiko; Namatame, Kazuhiko; Kitaura, Toyokazu; Kono, Chihiro; Goto, Mariko; Obinata, Takanobu; Furukawa, Naomichi Journal of Organic Chemistry, 1999 , vol. 64, # 9 p. 3190 - 3195

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Citation Number: 17

Abstract

The remote Pummerer reaction of the mono-sulfoxide of p-bis (methylthio)-aromatic 1 is described. The reaction of 1 with (CF3CO) 2O in CH2Cl2 gave a mixture of the corresponding mono-Pummerer product 2, the bis-Pummerer product 3, and the bis-sulfide 4 in an n: 1: 1 ratio (n≥ 2). The 1: 1 formation of 3 and 4 indicates an intermolecular interaction between sulfur atoms. The reaction with the deuterium-labeled 1-d 3 showed ...