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26.1.6.17.3 Method 3: Hydrolysis of α-Cyanodithiocarbamates

DOI: 10.1055/sos-SD-026-00205

Desmaële, D.Science of Synthesis, (200526371.

The use of cyanohydrin derivatives as masked acyl anion equivalents is very important, but in most cases the experimental procedures require the employment of strong bases, such as butyllithium, for the generation of the carbanion. However, α-cyanodithiocarbamates can be alkylated in aqueous media. For example, phase-transfer alkylation of the dithiocarbamate 291 in the presence of a catalytic amount of tetrabutylammonium iodide provides 292, which on treatment with excess sodium hydroxide in refluxing aqueous ethanol gives the corresponding ketone 293 (Scheme 78).[‌427‌]

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