ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Electrochemical Oxidation of Organic Compounds in Fluorosulfuric Acid. I. Voltammetric Investigation of ArylsulfofluoridesThe electrochemical oxidation of phenylsulfonylfluoride 1g and 16 of its alkylsubstituted derivates 1a-1g as well as a series of monomeric and dimeric products of the chemical oxidation of 1 were investigated by cyclic voltammetry in fluorosulfuric acid at -76°C. In all cases cation radicals could be detected as primary oxidation products. In further reaction steps one or two meta- or ortho-methyl groups are converted into fluorosulfonyloxymethyl groups. Depending on the stability of the cation radicals this process occurs either through an EEC-mechanism via the intermediate formation of dications (penta- and tetramethylsubstituted compounds) or through an ECE-mechanism with rate determining deprotonation of the cation radical.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19833250308
