Bulletin of the Chemical Society of Japan

Generation of sulfur ylides from sulfonium salts and their reactions. Comparative study of electrochemical reduction with the base method and mechanism elucidation …

Y Okazaki, F Ando, J Koketsu

Index: Okazaki, Yuichi; Ando, Fumio; Koketsu, Jugo Bulletin of the Chemical Society of Japan, 2003 ,  vol. 76,  # 11  p. 2155 - 2165

Full Text: HTML

Citation Number: 12

Abstract

The cathodic reduction of sulfonium salts in acetonitrile in the presence and absence of benzaldehyde was carried out. Results were compared with results of the base method. In the presence of benzaldehyde, the electrochemical reduction gave epoxides as a result of the Corey–Chaykovsky reaction, thus confirming ylide formation. The electrochemical reduction of sulfonium salts without benzaldehyde yielded rearrangement products in high ...