Tetrahedron p. 769 - 773 (1980)
Update date:2022-08-04
Topics:
Whitney, Richard R.
Jaeger, David A.
The effects of crown ethers (6 and 7) on the reactions of sodium (2a) and potassium enolates (2b) of 2-ethoxycarbonylcyclohexanone (1) with isopropyl iodide in dimethylsulfoxide and dimethoxyethane have been investigated. When the addition of crown ether promoted dissociation of ion pair 2 in either of the two solvents, the total rate of reaction (kt) increased and the ratio of carbon- (3) to oxygen-alkylation (4 and 5) products decreased. The results are consistent with the involvement of both the ion pair and more dissociated species in alkylation and with greater reactivity for the latter.
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Doi:10.1002/ardp.19803130709
(1980)Doi:10.1139/v80-224
(1980)Doi:10.1021/ic034893i
(2004)Doi:10.1021/jo01314a032
(1980)Doi:10.1021/jo00315a041
(1981)Doi:10.1016/j.tet.2004.03.015
(2004)
