Abstract
The reaction of phenylcyclopropane ( 1) with an excess of lithium and a catalytic amount of DTBB (2.5% molar) in THF at room temperature, followed by treatment with an electrophile [Me 3SiCl, PhMe 2SiCl, t-BuCHO, PhCHO, Me 2CO, Et 2CO, (CH 2) 5CO, adamantan-2-one, i-Pr 2CO, di(cyclopropyl)ketone] and final hydrolysis with water leads to allylic products 10 or 11 depending on the structure of the electrophile: whereas for chlorosilanes or crowded ketones γ-products 11 are isolated, for aldehydes and non-congested ketones α-products 10 are formed. The application of the same protocol to 1,1-diphenylcyclopropane ( 7) leads to a mixture of products 13– 15 resulting from the introduction of one or two electrophilic fragments to the open-chain mono- or dilithiated intermediate: also in this case the regiochemistry of the reaction is governed by steric reasons.
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