The mechanism of enol acetate hydroboration has been studied by examination of the hydroboration–protonolysis of cyclohex-1-enyl acetate. It has been shown that in this case the initial hydroboration proceeds not by exclusive β-addition of the boron to the enol acetate double bond but by both α- and β-addition modes. The mechanism has been further investigated by using perdeuteriodiborane.
B. C. Uff, M. E. Butcher, J. V. Adams, I. T. Streeting and J. W. Lewis, J. Chem. Soc., Perkin Trans. 1, 1974, 566 DOI: 10.1039/P19740000566
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