Halogen and Chalcogen Cation Pools Stabilized by DMSO. Versatile Reagents for Alkene Difunctionalization

Y Ashikari, A Shimizu, T Nokami…

Index: Ashikari, Yosuke; Shimizu, Akihiro; Nokami, Toshiki; Yoshida, Jun-Ichi Journal of the American Chemical Society, 2013 , vol. 135, # 43 p. 16070 - 16073

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Citation Number: 37

Abstract

Halogen and chalcogen cations (X+= Br+, I+, ArS+, and ArSe+) were generated by low- temperature electrochemical oxidation in the presence of dimethyl sulfoxide (DMSO) and were accumulated in the solution. DFT calculations indicated that DMSO stabilizes these cations by coordination. The complexes of I+ with one and two DMSO molecules were observed by cold-spray-ionization MS analyses. The stability of the resulting cation pools ...