Peroxidation of S-(2-Methyl-2-propyl) 2-Methyl-2-propanesulfinothioate

Article abstract of DOI:10.1021/jo00241a025

Oxidation of 1 equiv of S-(2-methyl-2-propyl) 2-methyl-2-propanesulfinothioate (1) with 2 equiv of m-chloroperoxybenzoic acid (MCPBA) gives S-(2-methyl-2-propyl) 2-methyl-2-propanesulfonothioate (4, 13percent), 2-methyl-2-propanesulfenic 2-methyl-2-propanesolfonic thioanhydride (5, 32percent), 2-methyl-2-propyl-3-chlorobenzoate (11, 4percent), 2-methyl-2-propyl 2-methyl-2-propanesulfinate (12, 22percent), and small amounts of bis(2-methyl-2-propyl) trisulfide (7) and bis(2-methyl-2-propyl) tetrasulfide (10).Possible mechanisms for product formation are discussed.