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Synlett 2001; 2001(12): 1929-1931
DOI: 10.1055/s-2001-18735
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The Synthesis of Bridged and Fused Ring Carbocycles Using a Novel Variation of an Intramolecular Nicholas Reaction

Elizabeth Tyrrell* , G. A. Skinner, Tahmina Bashir
  • *School of Chemical and Pharmaceutical Sciences, Kingston University, Penrhyn Road, Kingston KT1 2EE, U. K.; Fax: + 44(020)85477562; E-mail: e.tyrrell@kingston.ac.uk
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Publication Date:
04 December 2001 (online)

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A novel variation of an intramolecular Nicholas reaction is described that provides an efficient method for the synthesis of fused and bridged bicyclic compounds. The mechanism appears to involve an initial regioselective in situ double bond migration of a terminal alkene. The more stable disubstituted alkene then undergoes an intramolecular cyclisation reaction with a dicobalt hexacarbonyl stabilised cation. This transformation generates a second cation, which is subsequently quenched by a halide ion derived from the Lewis acid.

Nicholas reaction - dicobalt hexacarbonyl clusters - fused ring carbocycles - bridged ring carbocycles - double bond migration