Journal of the American Chemical Society

Reactions of the 2-Halo-3-(2-hydroxyethoxy) cyclohexenes with Potassium t-Butoxide in Dimethyl Sulfoxide1

AT Bottini, W Schear

Index: Bottini,A.T.; Schear,W. Journal of the American Chemical Society, 1965 , vol. 87, # 24 p. 5802 - 5803

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Citation Number: 4

Abstract

11 formed by prototropic rearrangement of 1 or 2. However, such a mechanism seems untenable because 3-isopropoxycyclohexene (12), 4 bp 79 (92 mm.), nZ4D 1.4448 (from 3- bromocyclohexene and isopropyl alcohol), is not converted to l-isopropoxycyclohexene (13) under the reaction conditions. 13 Note that failure to observe conversion of a 3- alkoxycyclohaxene to a 1-alkoxycyclohexene is not the result of an equilibrium that favors ...