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The utility of the cyanohydrin diethylphosphates derived from aldehydes (arylaldehydes, crotonaldehyde, and cinnamaldehyde) as an acyl anion equivalent was examined. Deprotonation of cyanophosphates with n-butyllithium in the presence of tetramethylethylenediamine in tetrahydrofuran at -78°C followed by reactions with alkyl (acyl) halides, carbonyl compounds, and α, β-unsaturated nitriles or esters, as well as cyanophosphates themselves, afforded alkylated (acylated) products, mixed benzoin and acyloin phosphates, polysubstituted cyclopropanes, and diarylfumaronitriles in moderate yields, respectively.
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Kurihara et al. (1987) studied this question.
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