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

Richard Francis Langler | Zendy; Z. A. Marini | Zendy; James A. Pincock | Zendy

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

Author(s) -

Richard Francis Langler,

Z. A. Marini,

James A. Pincock

Publication year - 1978

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v78-151

Subject(s) - sulfonyl , chemistry , sulfinic acid , sulfone , photodissociation , organic chemistry , medicinal chemistry , radical , alkyl

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%).

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