Stable Free Radicals. V. The Reaction between 1-Ethyl-4-carbomethoxypyridinyl and Benzyl Halides

Mahboob Mohammad, Edward M. Kosower

Research output: Contribution to journalArticlepeer-review

Abstract

The rates of reaction of the stable free radical, Py-, 1-ethyl-4-carbomethoxypyridinyl, with benzyl bromide and a number of benzyl chlorides (4-CH3O, 4-CH3, H, 4-C1, 4-NO2) have been measured in several solvents and, for the unsubstituted chloride and bromide, at several temperatures. The rate constant for the reaction of Py - with C6H5CH2C1 is little affected by substitution except for the 4-NO2 derivative, and the solvent effect on the rate is modest for C6H5CH2C1 and C6H5CH2Br. Criteria for decisions about the mechanisms of radical reactions are discussed and it is concluded that Py- reacts with benzyl chlorides and bromides (except for the 4-NO2 compound) in an atom-transfer reaction.

Original languageEnglish
Pages (from-to)2709-2713
Number of pages5
JournalJournal of the American Chemical Society
Volume93
Issue number11
DOIs
StatePublished - 1 Jun 1971
Externally publishedYes

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