Allylic carbonium ions. Part I. Acetolysis of 1,1- and 3,3-dimethylallyl 2,4-dinitrophenyl ether
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 10,p. 1157-1160
- https://doi.org/10.1039/p29760001157
Abstract
The 2,4-dinitrophenyl ethers of 1,1- and 3,3-dimethylallyl alcohol were prepared by convenient new arylation techniques, and their acetolysis rates and reaction products are reported. The tertiary isomer undergoes concurrent rearrangement to the primary isomer by a process of ion-pair return. Experiments relating these solvolyses to similar processes already described, involving other leaving groups and solvents, are reported.Keywords
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