Rhodium(I)-catalysed reactions of enynes. Linear coupling vs. cycloaddition
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1365-1369
- https://doi.org/10.1039/p19880001365
Abstract
The RhI-catalysed [2 + 2 + 2]-cycloaddition of dibut-2-ynyl ether (a 2,7-diyne) and acrylonitrile gives the corresponding bicyclic cyclohexadiene. Terminally unsubstituted 1,6-diynes fail to give an analogous reaction. Allyl propargyl ethers undergo a related RhI catalysed [2 + 2 + 2]-cyclodimerisation but substitution of the terminal alkene diverts the reaction to linear dimerisation involving the terminal alkyne. 4,9-Dioxadodec-1-ene-6,11-diyne gives a novel bicyclic triene by an unusual intramolecular RhI-catalysed [2 + 2 + 2]-reaction. The mechanisms of these various processes are discussed.Keywords
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