SourceEuropean Journal of Organic Chemistry, 2004, 1, (2004), pp. 74-83
Article / Letter to editor
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Synthetic Organic Chemistry
European Journal of Organic Chemistry
SubjectSynthetic Organic Chemistry
Reaction of functionalized 3,6-dihydro-2H-thiopyrans with N-iodosuccinimide in the presence of carboxylic acids results in the stereospecific formation of poly-functionalised thiolanes in good yield. The formation of these thiolanes is believed to proceed through either a nucleophilic or an electrophilic pathway leading to 4,5-cis-substituted derivatives. The use of unsymmetrical 2,2-substituted 3,6-dihydro-2H-thiopyrans gave mixtures of isomers that could be separated in several cases. From a 3-substituted thiopyran a 2,2,3,4,5-pentasubstituted thiolane was obtained. Attempts to use alcohols as external nucleophiles were unsuccessful with NIS, NBS, and N-bromoacetamide. Iodo-azidination with in situ generated IN3 was also unsuccessful. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
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