FORMAL HYDRIDE TRANSFER FROM NADH ANALOGS - 1-BENZYL-4-TERT-BUTYL-1,4-DIHYDRONICOTINAMIDE AS A MECHANISTIC PROBE

被引：58

作者：

ANNE, A

MOIROUX, J

SAVEANT, JM

机构：

[1] Laboratoire d'Electrochimie Moléculaire, Université de Paris 7, Unité Associée au CNRS No. 438, 75251 Paris Cedex 05

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 22期

关键词：

D O I：

10.1021/ja00075a043

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct and indirect (by means of ferrocene mediators) cyclic voltammetry and preparative-scale electrolyses of the title compound revealed that, even in the presence of bases, the resulting cation radical undergoes cleavage of the t-Bu. radical rather than proton abstraction. On the basis of this observation, the tert-butyl compound was used as a mechanistic probe, and it was shown that formal hydride transfer from t-BuBNAH to p-chloranil follows an electron-transfer reaction pathway. Implications for the hydride-transfer reactions of NADH analogues are discussed.

引用

页码：10224 / 10230

页数：7

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