Tetrahedron

Unexpected double benzylation of acetophenone under phase transfer catalysis conditions. Acidity or π− π interaction effect?

…, A Martínez-González, V Martínez-Merino, S Merino…

Index: Diez-Barra, Enrique; De la Hoz, Antonio; Loupy, Andre; Martinez-Gonzalez, Alfonso; Martinez-Merino, Victor; Merino, Sonia; Paugam, Renee; Sanchez-Verdu, Prado; Sansoulet, Jean; Torres, Jose Tetrahedron, 1997 , vol. 53, # 10 p. 3659 - 3668

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Citation Number: 11

Abstract

A π− π interaction in the transition state of the benzylation of 1, 3-diphenyl-1-propanone, the monobenzylation product of acetophenone, is proposed according to chemical, kinetic and theoretical approaches. Evidence for the existence of this kind of interaction in a transition state has been provided for the first time. The results obtained cannot be explained solely by the increased acidity but by considering the existence of a π-π interaction.