Oxidation of benzotrithiole analogues. Photochemical rearrangement of benzotrithiole 2-oxides to benzotrithiole 1-oxides involving intramolecular oxygen migration
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 17,p. 1995-2000
- https://doi.org/10.1039/p19930001995
Abstract
4,8-Dialkylbenzo[1,2-d;4,5-d′]bis[1,2,3]trithioles 2 were readily oxidized by m-chloroperbenzoic acid, N-bromosuccinimide and N-iodosuccinimide to form both benzobistrithiole 1 - and 2-oxides (4 and 5), and the ratio was dramatically affected by the kind of oxidizing agent used. Irradiation of the oxidized produts, benzobistrithiole 2-oxides 5, in acetonitrile with a high-pressure mercury lamp gave benzobistrithiole 1 -oxides 4 quantitatively. Photolysis of benzo- and naphtho-trithiole 2-oxides also yielded benzo- and naphtho-trithiole 1 -oxides. These photochemical oxygen migrations were shown to proceed intramolecularly via an excited singlet state by 18O-labelled, cross-over and triplet quencher experiments.Keywords
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