The photochemistry of benzylic sulfonyl compounds: The preparation of sulfones and sulfinic acids

Abstract

The photolysis of benzylic sulfonyl compounds (XSO 2 CH 2 Ph) gives products which are explained in terms of the chemistry of the benzyl and sulfonyl (XSO 2 •) radicals. The synthetic applications of this photocleavage have been examined for two general cases: (i) preparation of sulfones from disulfone precursors, R 1 SO 2 CHR 2 SO 2 CH 2 Ph to R 1 SO 2 CH 2 R 2 (yields ∼ 90%); (ii) preparation of sulfinic acids and sulfonyl chlorides from mono sulfone precursors, R 3 SO 2 CH 2 Ph to R 3 SO 2 H and R 3 SO 2 Cl (yields ∼ 55%).