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Oxidation of Diphenyl Sulfide by Singlet Oxygen Generated Carbonyl Oxides
Author(s) -
Agarwal Sudhir K.,
Murray Robert W.
Publication year - 1983
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198300058
Subject(s) - chemistry , singlet oxygen , benzophenone , photochemistry , sulfoxide , sulfide , electrophile , diazo , carbonyl sulfide , oxygen , singlet state , organic chemistry , sulfur , catalysis , physics , nuclear physics , excited state
Diphenyl sulfide has been oxidized to the sulfoxide by a series of 4,4′‐disubstituted benzophenone oxides. The carbonyl oxides were produced by photosensitized oxidation of the corresponding diazo compounds. Treatment of the data by a Hammett ρΣ approach indicates that the oxygen atom transfer is electrophilic in nature with ρ = +0.90. The results are discussed in terms of analogous reactions which are mediated by flavin‐dependent monooxygenase and particularly those oxidations believed to be involved in producing hepatotoxins.