Reactions of a metallacyclobutene complex with alkenes.
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.
Holland
Ryan L
RL
Department of Chemistry, University of California, San Diego, La Jolla, California 92093, USA.
Bunker
Kevin D
KD
Chen
Christopher H
CH
DiPasquale
Antonio G
AG
Rheingold
Arnold L
AL
Baldridge
Kim K
KK
O'Connor
Joseph M
JM