INTRAMOLECULAR ARYLSULPHOETHERIFICATION AND LACTONIZATION OF UNSATURATED ALCOHOLS AND CARBOXYLIC ACIDS INITIATED BY ANODIC OXIDATION OF DISULPHIDES

Article abstract of DOI:10.1016/S0040-4020(01)86141-X

The intramolecular sulphoetherification respectively sulpholactonization of alkenols and alkenoic acids can be initiated by addition of electrochemically generated sulphenyl cations starting from disulphides.The reaction can either be initiated by indirect electrochemical oxidation of diphenyldisulphide using bromide as redox catalyst or preferably by direct anodic oxidation of bis(4-methoxyphenyl)disulphide. 5- and 6-membered thioaryl substituted ethers and lactones thus may be generated starting preferably from mono or disubstituted alkenols and alkenoic acids.The reaction occurs as a trans-addition to the double bond while for endocyclic double bonds the new ring is cis-annelated.