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Synlett 1994; 1994(5): 363-365
DOI: 10.1055/s-1994-22855
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Ring Enlargement of Dichloromethylcyclohexadienones via Polystyrene-Supported Organotin Hydride

Dirk P. Dygutsch* , Wilhelm P. Neumann, Markus Peterseim
  • *Department of Chemistry, University of Dortmund, D-44221 Dortmund, Germany
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Publication Date:
22 March 2002 (online)

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The ring-enlargement of dichloromethylcyclohexadienonederivatives to tropone nuclei via organotin hydrides has been expanded and improved. It can be performed without contamination of the product with toxic tin by-products. The employed polymer-supported organotin hydride and its consecutive products can easily be separated from reaction mixtures by simple filtration. Examples of methyl- and benzotropones are given. The yield of the synthesis via polystyrene-supported organotin hydrides has been compared with those of the formation via tri-n-butyltin hydride (TBTH).