102107-90-4Relevant articles and documents
Electro-organic Reactions. Part 24. Preparative and Mechanistic Aspects of the Anodic Oxidation of Dithioacetals and 1,3-Dithianes
Porter, Quentin N.,Utley, James H. P.,Machion, Pedro D.,Pardini, Vera L.,Schumacher, Paolo R.,Viertler, Hans
, p. 973 - 979 (2007/10/02)
Anodic oxidation of the title compounds is a convenient and efficient method for deprotection, i.e. for the regeneration of carbonyl compounds. A detailed investigation of sulphur-containing products confirmed that the initial, 2 F mol-1, products are disulphides which, in aqueous acetonitrile, are oxidised further to alkyl alkane thiosulphinates and the corresponding thiosulphonates.In some cases alkyl polysulphides and N-alkylacetamides are important products.Unsymmetrical dithioacetals are oxidised anodically to the three possible disulphides, i.e. cross-coupling occurs.Unsymmetrical disulphides are similarly oxidised to a complex mixture of symmetrical and unsymmetrical thiosulphinates and thiosulphonates. These results, combined with those of cyclic voltammetric and coulometric experiments, suggest a mechanism in which the key step in carbon-sulphur bond cleavage in the initially formed radical cation.The direction of the cleavage is determined by understandable substituent effects.
