Prevalence of cis-addition products in the reaction of the butenyl Grignard reagent with sterically hindered ketones

RA Benkeser, WG Young, WE Broxterman…

Index: Benkeser,R.A. et al. Journal of the American Chemical Society, 1969 , vol. 91, # 1 p. 132 - 137

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Citation Number: 43

Abstract

Abstract: The reactions of crotylmagnesium bromide with ethyl isopropyl, diisopropyl, isopropyl t-butyl, and di-t-butyl ketones have been examined under carefully controlled conditions. The quantity of a-methylallylcarbinol formed in each case was found to decrease and the amount of crotylcarbinol to increase progressively as the steric requirements of the alkyl groups attached to the carbonyl of the ketone increased. This observation probably ...