Electrolytic reactions of fluoro organic compounds. 9. Fluoride ion promoted anodic substitutions of chalcogeno compounds. 1. Regioselective anodic alkoxylation of …

T Fuchigami, H Yano, A Konno

Index: Fuchigami, Toshio; Yano, Hidetoshi; Konno, Akinori Journal of Organic Chemistry, 1991 , vol. 56, # 24 p. 6731 - 6733

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Abstract

Summary: Anodic a-alkoxylation of sulfides was remarkably promoted in the presence of fluoride ions: When Et8N. 3HF was used as a supporting electrolyte, simple alkyl phenyl sulfides and sulfides bearing weak electronwithdrawing groups underwent anodic alkoxylation via fluorosulfonium ions as key intermediates in a unique Pummerer-type mechanism with reasonable or high yields for the first time.