Electrolytic partial fluorination of organic compounds. Part 29. Anodic mono- and difluorination of 2-benzoxazolyl sulfides

Anodic fluorination of 2-benzoxazolyl sulfides using various fluoride salts and dimethoxyethane as a supporting electrolyte and a solvent, respectivel y, resulted in the formation of the corresponding mono- and difluorinated p roducts in reasonable yields. The monofluorination took place selectively a t the position alpha to the sulfur atom while the difluorination resulted a t both the alpha-position and the benzene ring while the expected alpha,alp ha-difluorination did not take place at all. Moreover, anodic fluorination of the electrolytic solvent, DME, which has never been reported so far, was also observed as a side-reaction and this fluorination was further confirm ed by carrying out anodic fluorination of DME itself in the absence of a su bstrate sulfide. (C) 1999 Elsevier Science S.A. All rights reserved.