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Reactivity of the >P-O− nucleophiles toward arylmethyl chloride systems*†

✍ Scribed by Dariusz Witt; Tadeusz Ossowski; Janusz Rachon

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
219 KB
Volume
10
Category
Article
ISSN
1042-7163

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✦ Synopsis

The reactions of sodium dimethyl and diisopropyl phosphite, as well as dibenzylphosphinite with 4-nitrobenzyl chloride, 9-chlorofluorene, and diphenylchloromethane were studied in detail by the isolation and identification of all the products, and the examination of the effects of the solvents on the product distribution. The results of the performed experiments are compatible with the proposed mechanism: a ϾP-O ‫מ‬ anion acts toward an arylmethyl chloride as a base and abstracts a proton to form a carbanion, which can then participate in the SET processes to produce carbon-centered radicals. Additionally, the ϾP-O ‫מ‬ reagent can act as a carbon-centered radical trap if it is present in a high enough concentration.

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