Photochemical Conversion of Sulfonium Salts via a 1,3-Sigmatropic Rearrangement. Photogeneration of Broensted Acids

Article abstract of DOI:10.1021/jo00222a031

A series of 1-naphthyl methyl-substituted alkylsulfonium salts underwent 1,3-sigmatropic rearrangements to form 1-(methylthio)-2-substituted alkylnaphthalenes and the corresponding acid with quantum yields between 0.24 and 0.10.In competition with rearrangement was a bond-cleavage reaction forming 1-naphthyl methyl sulfide.The quantum yield for bond cleavage was ca. 0.15 for all the compounds studied.