Regioselective Metalation of Phenylcyclopropane and Smooth Addition of 1-Phenylcyclopropyl Potassium onto Ethylene

Article abstract of DOI:10.1002/hlca.19800630833

Whereas pentyl sodium in pentane mainly promotes a hydrogen/metal exchange reaction at the m- and p-position of phenylcyclopropane, both the butyllithium/potassium t-butoxide reagent and trimethylsilylmethyl potassium in tetrahydrofuran convert phenylcyclopropane exclusively into 1-phenylcyclopropyl potassium.The latter organometallic derivative adds smoothly onto the double bond of ethylene at temperatures around -40 deg.