Deuterium labelling studies have shown that the facile elimination of the 5β-hydroxy group observed in the course of hydroboration of a 5β-hydroxyandrost-3-ene may involve a trans diaxial borane-borinate elimination coupled with a syn transfer of hydrogen from the borinate.
J. R. Hanson, M. D. Liman and C. Uyanik, J. Chem. Res. (S), 1998, 126 DOI: 10.1039/A708181B
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