Process for substituting a hydrocarbon group

A process for substituting a hydrocarbon group from a cuprate complex to an expoxide, .alpha.,.beta.-unsaturated Ketone or an alkyl halide, tosylate or mesylate through a carbon to carbon bond comprising preparing a higher order cuprate complex by bringing into reactive contact a first cuprate complex of the formula:

• ##STR28## wherein (a) X is --CN, --SCN, --OSO.sub.2 CF.sub.3, or --S--phenyl;
• (b) each R is independently lower alkyl, alkenyl, phenyl, naphthyl, phenanthryl, or thienyl, provided that (i) each of the aforementioned radicals may be substituted with non-interferring substituents and (ii) only one R in the first cuprate complex may be alkenyl, phenyl, naphthyl, phenanthryl, or thienyl;
• and
• (c) each R.sup.1 is independently lower alkyl;
• with a stannane compound of the formula:
• R.sub.t Sn(R.sup.2)3
• wherein R.sub.t is a carbanion for carbon to carbon bond formation reactions and is different from any R in the first cuprate complex and each R.sup.2 is independently lower alkyl or R.sub.t ;
• whereby R.sub.t replaces at least one R on the first cuprate complex to form a higher order cuprate complex;
• and
• reacting said higher order cuprate complex with an .alpha.,.beta.-unsaturated ketone, an epoxide, or an alkyl halide, tosylate or mesylate to substitute R.sub.t to the epoxide, .alpha.,.beta.-unsaturated ketone, alkyl halide, tosylate or mesylate.