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Premium Ring Contraction of 3,6‐Dihydro‐2 H ‐thiopyrans to Thiolanes by an Iodo‐Oxyacylation Reaction
Lucassen Andre C. B.,
Zwanenburg Binne
Publication year2004
Publication title
european journal of organic chemistry
Resource typeJournals
PublisherWILEY‐VCH Verlag
Abstract Reaction of functionalized 3,6‐dihydro‐2 H ‐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‐2 H ‐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 IN 3 was also unsuccessful. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Subject(s)catalysis , chemistry , electrophile , materials science , medicinal chemistry , metallurgy , nucleophile , organic chemistry , reaction conditions , ring (chemistry) , stereochemistry , stereospecificity , yield (engineering)
SCImago Journal Rank0.825

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