Regioselective Addition of Stannylcyanocuprates to Acetylenic Ethers: A Chemical and Spectroscopic Study

Jorge A. Cabezas; Allan C. Oehlschlager

doi:10.1055/s-1994-25492

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Synthesis 1994; 1994(4): 432-442
DOI: 10.1055/s-1994-25492

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Regioselective Addition of Stannylcyanocuprates to Acetylenic Ethers: A Chemical and Spectroscopic Study

Jorge A. Cabezas^* , Allan C. Oehlschlager

^*Department of Chemistry, Simon Fraser University Burnaby, British Columbia, V5A 1S6, Canada

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Publication Date:
17 September 2002 (online)

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The reactions of acetylenic ether 1 with higher order cuprates 2a, 2b and 2c were studied chemically and spectroscopically. Conditions were developed to efficiently and regioselectively prepare α- and β-stannylvinyl ethers. ¹H and ¹³CNMR studies of these reactions suggest that in the presence of HMPA, higher order stannylcyanocuprate, (Bu₃Sn)₂Cu(CN)Li₂, 2a, exists in equilibrium with Gilman cuprate, (Bu₃Sn)₂CuLi.

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