Ring Openings of Substituted Cyclobutanes Induced by Grignard Reagents. I. Methyl 2-Dimethylamino-3, 3-dimethylcyclobutanecarboxylate

L Weintraub, A Wilson, DL Goldhamer…

Index: Weintraub,L. et al. Journal of the American Chemical Society, 1964 , vol. 86, p. 4880 - 4885

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Citation Number: 10

Abstract

Reaction of methyl 2-di1nethylamino-3, 3-dimethylcyclobutanecarbox~ late (I) with phenylmagnesium bromide does not produce the expected diphenyl (2-dimethylami1io-3, 3- dimethyl) cyclobutylcarbinol(11). The product is instead shown to be 1, 5-diphen~ l-4, 4- dimethyl-5-dimethylaminopentanone-l resulting from ring cleavage and addition of a Grignard radical to the p-carbon atom. The ring-opening reaction is completely general for ...