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Mechanism of the reaction of diphenylphosphinodithioic acid with nitriles

โœ Scribed by Steven A. Benner

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

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โœฆ Synopsis

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 thioamides under mild conditions.

1 We have studied the kinetics of this process, and wish to report here evidence that the reaction proceeds via the reaction mechanism shown below. The first step is especially interesting, as it appears to be an "en," reaction involving the participation of no fewer than four heteroatoms.

๐Ÿ“œ SIMILAR VOLUMES

Diphenylphosphinodithioic acid: A reagen
Diphenylphosphinodithioic acid: A reagent for the conversion of nitriles to thioamides
โœ Steven A. Benner ๐Ÿ“‚ Article ๐Ÿ“… 1981 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 206 KB

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

The reaction of nitriles with O,O-dialky
The reaction of nitriles with O,O-dialkyldithiophosphoric acids
โœ N.M. Yousif ๐Ÿ“‚ Article ๐Ÿ“… 1989 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 259 KB

Nitrlles react with dlslkyldithlophosphorlc acids za-c to give a mixture of corresponding thiosmldes and O,Odlalkyl-N-thioaceyl-phosphoroamldothloates ?a-e. The structure of compounds 1 are elucidated chemically and from electronic spectra. The yield of thloamides are improved from the reactlon of n