A highly stereoselective generation and trapping of 1,2-dichloro-3-methyl-4-phenylbut-2-enylidene
Abstract
3-Benzyl-1,2-dichloro-3-methylcyclopropene undergoes an apparent cyclopropene to vinylcarbene rearrangement at 20 °C; one stereoisomer of the derived vinylcarbene is trapped selectively in either intra- or inter-molecular processes, and in the latter case trapping by addition to the alkene bond of methyl methacrylate leads to a cyclopropane with vinyl and ester groups cis-related. The stereochemistries of the products of both inter- and intea-molecular processes have been established by X-ray crystallography.
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