Reactions of Organometallic Reagents with 2-Hydroxymethylenecyclohexanone and Its Isopropyl Ether1, 2

AS Dreiding, SN Nickel

Index: Dreiding; Nickel Journal of the American Chemical Society, 1954 , vol. 76, p. 3965,3967

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Citation Number: 12

Abstract

The condensation of three organometallic reagents (methylmagnesium iodide, methyllithium and phenylmagnesium bromide) with 2-hydroxymethylenecyclohexanone (I) resulted in 2- alkylidenecyclohexanones (IV and V), presumably by a nucleophilic attack at the hydroxymethylene carbon of the intermediate enolate salt 11. The isopropyl ether of 2- hydroxymethylenecyclohexanone (VII) underwent mostly 1, 4-addition with ...