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

被引：11

作者：

DiezBarra, E

delaHoz, A

Loupy, A

MartinezGonzalez, A

MartinezMerino, V

Merino, S

Paugam, R

SanchezVerdu, P

Sansoulet, J

Torres, J

机构：

[1] UNIV PARIS 11, URA 478 CNRS, F-91405 ORSAY, FRANCE

[2] UNIV PUBL NAVARRA, DEPT QUIM, PAMPLONA 31006, SPAIN

来源：

TETRAHEDRON | 1997年 / 53卷 / 10期

关键词：

D O I：

10.1016/S0040-4020(97)00089-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A pi-pi 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 pi-pi interaction. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：3659 / 3668

页数：10

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