Cyclopropylbenzene ring opening by chlorine atom: radicals or radical ions?

Cyclopropylbenzene radical chlorination leads to hydrogen atom ion and to ring opening. The contribution of the last process is increased in the presence of acids and in polar solvents. It is suggested that the ring opening process proceeds via radical cation formation by single electron transfer fr...

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Bibliographic Details
Published in:Journal of physical organic chemistry 2003-03, Vol.16 (3), p.189-193
Main Authors: Trukhin, Aleksei V., Eliseenkov, Evgeny V., Dneprovskii, Aleksei S.
Format: Article
Language:English
Subjects:
free radical chlorination
mechanism
radical cations
ring opening
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Summary:Cyclopropylbenzene radical chlorination leads to hydrogen atom ion and to ring opening. The contribution of the last process is increased in the presence of acids and in polar solvents. It is suggested that the ring opening process proceeds via radical cation formation by single electron transfer from cyclopropylbenzene to the chlorine atom in the first stage of reaction. Copyright © 2003 John Wiley & Sons, Ltd.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.589