On the mechanism of addition of lithium pinacolone enolate to benzaldehyde: Polar or electron transfer?

H Yamataka, D Sasaki, Y Kuwatani…

Index: Yamataka, Hiroshi; Sasaki, Daizo; Kuwatani, Yoshiyuki; Mishima, Masaaki; Tsuno, Yuho Journal of the American Chemical Society, 1997 , vol. 119, # 42 p. 9975 - 9979

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Citation Number: 19

Abstract

The carbonyl-carbon kinetic isotope effect (KIE) and the substituent effect were measured for the reaction of lithium pinacolone enolate (CH2 C (OLi) C (CH3) 3) with benzaldehyde, and the results were compared with those for other lithium reagents such as MeLi, PhLi, and CH2 CHCH2Li. Ab initio MO calculations (HF/6-31+ G*) were carried out to estimate the equilibrium IE on the addition to benzaldehyde. A carbonyl addition reaction, in general, ...

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