Reactions of a Metallacyclobutene Complex with Alkenes
Journal of the American Chemical Society2008Vol. 130(31), pp. 10093–10095
Citations Over TimeTop 19% of 2008 papers
Ryan L. Holland, Kevin D. Bunker, Christopher H. Chen, Antonio G. DiPasquale, Arnold L. Rheingold, Kim K. Baldridge, J. M. O’Connor
Abstract
The first productive reactions of a characterized metallacyclobutene complex with alkenes are reported. Thus, the metallacyclobutene complex (eta5-C5H5)(PPh3)Co[kappa2-(C,C)-C(SO2Ph) C(Si(CH3)3)CH(CO2CH2CH3)] (2) undergoes reaction with alkenes to give 1,4-diene complexes with a high degree of regio- and stereoselectivity. A mechanism is proposed in which the metallacyclobutene generates a cyclic vinylcarbene intermediate that undergoes [4 + 2]-cycloaddition reactions with activated alkenes. A model of the vinylcarbene intermediate has been examined using quantum mechanical methods.
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