0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content. 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]

Meeeee 88 Meeeeee eeee α-Meeeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee 888 ee Meeeeeee ee eee α-Meeeeeeeeeeeeeeeeeee Meeee; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eee eeeeeeeeeeeeeee 888 (8 eeeee) eee MeMM (88 eeeee) ee 88% ee MeMM eee eeeeeeee eee 88e. Meeee eeeeeee, eee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeeee eeee eeeeee eeee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee).