Photochemical carbon - sulfur bond cleavage in some alkyl and benzyl sulfides

SERGIO M. BONESI, MAURIZIO FAGNONI, DANIELE DONDI, ANGELO ALBINI

INORGANICA CHIMICA ACTA

Elsevier

Lugar: Netherland; Año: 2007 vol. 360 p. 1230 - 1234

0020-1693

Irradiation (254 nm) of five alkyl and benzyl ethyl sulfides causes efficient(fr 0.27-0.90) homolytic cleavage of the C-S bond. Of the resulting fragments, thiyl radicals mainly couple, with alkyl radicals abstract hydrogrn, disproportionate or couple when stabilized (benzyl). Selective trapping of ethier of the two types of radicals occurs in the presence of nucleophilic (methyl vinyl ether and 1-hexene) and respectively, electrophilic (acrylonitrile) alkenes. When an easily oxidized radical is formed, e.g. cumyl, secondary electron transfer leads to the corresponding cation.