Tetrahedron

Conjugate addition of grignard reagents to unsaturated ketones: gc/ms-hplc study. Isolation and oxidation of e and z enols of a ketone

AG Pinkus, S Logaraj

Index: Pinkus, A. G.; Logaraj, S. Tetrahedron, 1988 , vol. 44, # 22 p. 6801 - 6806

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Abstract

The conjugate addition of phenylmagnesium bromide to benzalacetoinesitylene (1) was studied. The only product resulting from 1, 4-addiaon was Kohler's ketone (4) in 84±1% yield based on (1) by isolation and analysis. The byproducts from 4 were formed mainly by oxidation of the Z enol of 4 to the α-ketohydroperoxide (6) during the hydrolysis and workup of the product followed by subsequent decomposition of 6 to diphenylethanal and a trace ...