90953-82-5Relevant articles and documents
Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions
Liu, Kai-Jian,Deng, Ji-Hui,Yang, Jie,Gong, Shao-Feng,Lin, Ying-Wu,He, Jun-Yi,Cao, Zhong,He, Wei-Min
, p. 433 - 438 (2020)
The development of eco-friendly and switchable catalytic systems for the conversion of a sole raw-material into distinct high-value products is a particularly attractive concept and a daunting synthetic challenge. In the present work, the first example of efficient and selective oxidation of sulfides to sulfones and sulfoxides using molecular oxygen under clean conditions was established.
Remote Pummerer Reaction via Intermolecular Through-Space Interaction between Sulfonium and Sulfenyl Sulfur Atoms
Kobayashi, Kenji,Koyama, Emiko,Namatame, Kazuhiko,Kitaura, Toyokazu,Kono, Chihiro,Goto, Mariko,Obinata, Takanobu,Furukawa, Naomichi
, p. 3190 - 3195 (2007/10/03)
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-d3 showed that the formation of 2 occurs at the sulfenyl as well as sulfinyl groups in 1a-d3-1d-d3, in which the product ratio of 2-d3:2-d2 is in the range of 3.5-10. On the other hand, the Pummerer reaction of 1e-d3 occurred preferably at the sulfinyl group in a usual manner. The reaction of a 1:1 mixture of the bis-sulfide 4 and the bis-sulfoxide 5 with (CF3-CO)2O also gave 2, 3, and 4 in a ratio similar to that for the reaction of 1. The mechanism in the present remote Pummerer reactions is discussed in light of an intermolecular through-space interaction between the sulfonium and sulfenyl sulfur atoms, and a dithia dication dimer B and/or a bis(dithia dication) cyclic dimer C are proposed as intermediates.