A Stereoselective α-Hydroxylation of Cyclohexanecarbonitriles

References

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• For example, cyanohydrins of diaryl ketones can be prepared from diarylacetonitriles but not from diaryl ketones. Cyanohydrins of aldehydes can be prepared from aldehydes but not from primary nitriles
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• The α-peracetoxynitriles 5, and 6 were prepared according to reference 1 and were separable by chromatography on Merck silica gel F254 in 1:3 ether-hexane and had ir spectra showing a characteristic C=O absorption (5.59 and 5.64 (sh) μ). The isomers were best distinguished by nmr (CDCl3): 5 had δ 0.90 (s, 3, C(CH3)3) and 2.14 (s, 3, COCH3); 6 had δ 0.87 (s, 3, C(CH3)3) and 2.16 (s, 3, COCH3)
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• This agrees with a literature report in which 2 afforded a 75:25 mixture of 3 and 4 (reference 4)
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• We would like to thank the Colorado Heart Association and the Natioanl institutes of Health (GM 22978–01) for their generous financial support
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