Fluoroacetamidation, electrochemical

Electrochemical oxidation of 1,2-dihydronaphthalene or an indene in acetoni-tnle containing triethylamine tris(hydrogen fluoride) provides a mixture of tereoisomeric difluorides and vicinal fluoroacetamides [201] (equation 38)... 

Moreover, the electrochemical fluoroacetamidation of cycloalkenes was carried out in acetonitrile with tetraethylammonium fluoride/hydrofluoric acid, in order to obtain fluoroac-etamides 16 and 17, although in low yield. cw-Compounds are the major components of the reaction mixture, as determined by H NMR. This result was ascribed to the acetonitrile addition to the /1-fluorocarbocation absorbed on the electrode surface185-186. 

Electrochemical fluoroacetamidations of 1-alkylindene were investigated by Laurent s group. The stereoselectivities with respect to F/alkyl and F/MeCONH introduction were found to be mainly trans and cis, respectively. In contrast, Yoneda and his co-workers found that anodic oxidation of cyclic unsaturated esters in EtjN-SHF resulted... 

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