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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Selective formation of angular tricyclic compounds by ruthenium-mediated ring-rearrangement metathesis
Fuye Gao1, Craig T M Stamp, Paul D Thornton
1Department of Chemistry, Dalhousie University, P. O. Box 15000, Halifax, Nova Scotia, Canada B3H 4R2.
Abstract:
Unsaturated spirocyclic substrates bearing two alkenyl chains underwent ruthenium-mediated ring-rearrangement metathesis through relaying cyclohexene and cycloheptene moieties to give angularly fused tricyclics. In some instances where two products were expected, high degrees of selectivity were observed. In one instance the structural parameter leading to selectivity was very subtle; in others the transformation favoured the formation of products with a cis-fused cyclohexene moiety. An unusual transformation involving ring-opening, double-bond migration, and then ring-closing was observed.
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