Organic synthesis using a migrating functional group: [1,2] and [1,3] phenylthio shifts in synthesis via allyl sulphides

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 alcohols