The Stereochemistry of Organometallic Compounds. XXII The Stereochemistry of Metal-Catalysed Hydrogen Cyanide Addition to Olefins

W. Roy Jackson, Craig G. Lovel

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Reactions of (E)-3, 3-dimethyl(l, 2-D2)but-1-ene with hydrogen cyanide and of (E)-3, 3-dimethyl-(1-D)but-1-ene with deuterium cyanide have been shown to proceed in a completely stereospecific cis fashion when a catalyst system based on Pd(diop)2 was used. Reaction between 4-t-butylcyclo-hexene and deuterium cyanide with the catalyst system gave only the equatorial nitriles trans-4-t-butylcyclohexane-1-carbonitrile and cis-3-t-butylcyclohexane-1-carbonitrile with cis incorporation of deuterium. Use of a catalyst system based on Ni[P(OPh)3]4and zinc chloride led to significant amounts of isotopic exchange and rearrangement. These results are compared with those from hydroformylation of the olefins, and the mechanism of hydrocyanation is discussed.

Original languageEnglish
Pages (from-to)2053-2067
Number of pages15
JournalAustralian Journal of Chemistry
Issue number10
Publication statusPublished - 1 Jan 1982

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