Abstract
The rate of the reaction between the anion of 1,4-dihydro-4-methoxycarbonyl-1-methylpyridine (1- and sterically hindered alkyl halides, and between the perylene dianion (Pe2-) and t-butyl chloride and sec-butyl bromide has been measured by electrochemical techniques. The rate was found to be close to the rate of single electron-transfer (SET) from anion radicals (A{minus sign, dot below}) with the same standard potential as 1•/1-, resp. Pe{minus sign, dot below}/Pe2- to the corresponding alkyl halides. The kinetic results strongly suggest that a SET mechanism is the rate-determining step in these nucleophilic substitutions.
Originalsprog | Engelsk |
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Tidsskrift | Tetrahedron Letters |
Vol/bind | 27 |
Udgave nummer | 1 |
Sider (fra-til) | 95-98 |
Antal sider | 4 |
ISSN | 0040-4039 |
DOI | |
Status | Udgivet - 1986 |
Udgivet eksternt | Ja |