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

✍ Scribed by Enrique Díez-Barra; Antonio de la Hoz; André Loupy; Alfonso Martínez-González; Víctor Martínez-Merino; Sonia Merino; Renée Paugam; Prado Sánchez-Verdú; Jean Sansoulet; José Torres


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
432 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis


A n-n interaction in the transition state of the benzylation of 1,3-diphenyl-1propanone, 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 ~-n interaction.