High-yield synthesis of nitriles by oxidation of aldehyde N,N-dimethylhydrazones with dimethyldioxirane

被引：22

作者：

Altamura, A ^{[1
]}

D'Accolti, L ^{[1
]}

Detomaso, A ^{[1
]}

Dinoi, A ^{[1
]}

Fiorentino, M ^{[1
]}

Fusco, C ^{[1
]}

Curci, R ^{[1
]}

机构：

[1] Univ Bari, Ctr MISO, CNR, Dipartimento Chim, I-70126 Bari, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 14期

关键词：

dioxiranes; oxidation; N; N-dialkylhydrazones; nitriles;

D O I：

10.1016/S0040-4039(98)00118-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using dimethyldioxirane, the selective transformation of aldehyde N,N-dimethylhydrazones into the corresponding nitriles was achieved in high yield and under mild conditions. The determination of the substituent effect an rates, along with an estimate of the primary kinetic isotope effect using PhCH-NNMe2 and PhCD=NNMe2 provided useful hints concerning the reaction mechanism. It was also observed that the nitrile products do not undergo further oxidation, even with excess dioxirane. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2009 / 2012

页数：4