Tetrahedron p. 6295 - 6304 (1988)
Update date:2022-08-05
Topics:
Pike, Philip
Hershberger, Susan
Hershberger, James
The reductive alkylation of acrylonitrile and of 2-cyclohexen-1-one by alkyl halides using tributylgermanium hydride was systematically evaluated.The performance of the germanium reagent was compared to that of the more commonly employed tributyltin hydride.For certain applications thegermanium reagent afforded improved yields without the use of large excess olefin concentrations.Disadvantages of the germanium reagent include a tendency to hydrogermylate active terminal olefins and a general low reactivity towards alkyl halide substrates.The following series of six other triorganotin and triorganogermanium hydrides were also briefly screened for possible application to reductive alkylations: trimesityltin hydride, trimesitylgermanium hydride, triphenyltin hydride, triphenylgermanium hydride, trineopentyltin hydride, and tricyclohexylgermanium hydride.
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