Electrochemical synthesis of 3-phenylcinnamonitrile by reduction of benzophenone in acetonitrile

被引：12

作者：

Batanero, B

Sánchez-Sánchez, CM

Montiel, V

Aldaz, A

Barba, F ^{[1
]}

机构：

[1] Univ Alcala de Henares, Dept Organ Chem, Madrid 28871, Spain

[2] Univ Alicante, Dept Chem Phys, E-03080 Alicante, Spain

来源：

ELECTROCHEMISTRY COMMUNICATIONS | 2003年 / 5卷 / 04期

关键词：

benzophenone; 3-phenylcinnamonitrile; reduction mechanism; radical-anion; cyclic voltammetry;

D O I：

10.1016/S1388-2481(03)00066-3

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

The electrochemical cyanomethylation of benzophenone in acetonitrile was investigated as an interesting way of synthesizing high yield of 3-phenylcinnamonitrile (55% for 50% of theoretical circulated charge). This synthetic method uses the benzophenone radical-anion as a strong electrogenerated base to abstract a proton from the solvent and obtain the nucleophile -CH2CN. This anion is capable of yielding cyanomethylated products very easily. In our case the reaction of this anion with benzophenone yields 3-phenylcinnamonitrile in a father-son like mechanism. (C) 2003 Elsevier Science B.V. All rights reserved.

引用

页码：349 / 353

页数：5