Organic synthesis using a migrating functional group: [1,2] and [1,3] phenylthio shifts in synthesis via allyl sulphides
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 1131-1141
- https://doi.org/10.1039/p19770001131
Abstract
2-Hydroxyalkyl phenyl sulphides, readily available via alkylation of 2-(phenylthio)-ketones and -nitriles, undergo acid-catalysed dehydration to allyl phenyl sulphides, during which [1,2] phenylthio migration occurs, followed in some cases by a light-, heat-, or acid-induced [1,3] phenylthio shift. The versatility of such allyl phenyl sulphides as synthons is demonstrated by their alkylation with alkyl halides and carbonyl compounds and transformation into allyl alcoholsKeywords
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