Photodecomposition of alkyl benzoates and S-alkyl thiobenzoates. Possibility of a barton-type transition state
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1244-1247
- https://doi.org/10.1039/p19730001244
Abstract
U.v. irradiation of alkyl (C3–C5) benzoates under nitrogen gives mainly benzoic acid (ca. 40%), via a Norrish type II process, along with benzaldehyde (< 4%) and other products. In the case of pentyl benzoate, a small amount of propiophenone (1·6%) was obtained. In contrast, S-pentyl thiobenzoate gives mainly benzaldehyde (27%)(via a Norrish type I process), dipentyl disulphide (23%), and some other minor products, viz, biphenyl (1·4%), pentyl phenyl sulphide (3·2%), pentylbenzene (trace), and propiophenone (trace), but no thiobenzoic acid. Electron impact-induced fragmentation of these alkyl benzoates and of S-alkyl thiobenzoates correlates with their photochemical behaviour; 50–60% benzoic acid cation radical was obtained from alkyl benzoates, but only ca. 5% thiobenzoic acid cation radical from S-pentyl thiobenzoate.Keywords
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