REACTIONS OF ORGANOMAGNESIUM COMPOUNDS WITH ALPHA, BETA-UNSATURATED KETONES, PART 1. REACTIONS OF ORGANOMAGNESIUM COMPOUNDS WITH SATURATED KETONES, PART 2
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The reactions of trans-4-phenyl-buten-2-one and trans-3-penten-2-one with dimethyl-, diethyl- and dipenylmagnesium were studied. The ratio of conjugate to normal addition observed was decreased only slightly by the presence of Magnesium bromide in the reaction mixture. In the reaction with ketone with DIETHYLMAGNESIUM, VARIATIONS IN THE CONCENTRATION OF EITHER REACTANT DID NOT SIGNIFICANTLY ALTER THE PROPORTIONS OF NORMAL AND CONJUGATE ADDITION PRODUCTS. THE PRESENCE OF CUPROUS IONS FAVORED CONJUGATE ADDITION BOTH WITH THE DIARYL- AND DIALKYL-MAGNESIUM AN WITH Grignard reagents. The presence of excess isoprene in the reaction mixtures did not reduce the proportion of conjugate addition. The reactions of 3-pentanone and 2-4-dimethyl3-pentanone with diethyl- and alkoxyethylmagnesium were studied. The RATIO OF ENOLIZATION AND REDUCTION TO NORMAL ADDITION was significantly decreased by the presence magnesium bromide in the reaction mixture. Kinetic data for these reactions was obtained.
- Organic Chemistry