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Diphenylphosphinodithioic acid: A reagent for the conversion of nitriles to thioamides

✍ Scribed by Steven A. Benner

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
206 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

Diphenylphosphinodithioic acid is a reagent useful for a sequence effecting the hydrolysis of nitriles under mild conditions. Of all functional groups at the acyl level of oxidation, nitriles are the most resistant to reaction. The poor electrophilicity of the carbon combined with the weak basicity of the nitrogen makes the nitrile group immune to attack under all but the harshest of conditions. Thus, existing procedures for the hydrolysis of nitriles call for either strong acid or strong base, and often

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Kinetic studies of the reaction of diphenylphosphinodithioic acid with nitriles support a two step mechanism, the first step being an "ene" reaction. In the preceeding communication we described the use of diphenylphosphinodithioic acid (1) as a reagent for the rapid conversion of nitriles to thioa

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