The hydrogenolysis of 3β-p-tolylsulphonyloxyandrost-5-en-17-one with lithium aluminium deuteride and of 3β-iodoandrost-5-en-17-one with zinc-[2H]acetic acid has been shown by 2H n.m.r. spectroscopy not to be stereospecific, contrary to earlier reports.
J. R. Hanson, H. J. Wadsworth and W. E. Hull, J. Chem. Soc., Perkin Trans. 1, 1980, 1381 DOI: 10.1039/P19800001381
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