Oxime Ether Radical Cations Stabilized by N-Heterocyclic Carbenes

被引：26

作者：

Kim, Youngsuk ^{[1
,2
]}

Kim, Kimoon ^{[1
,2
,3
]}

Lee, Eunsung ^{[1
,2
,3
]}

机构：

[1] Ctr Self Assembly & Complex, IBS, Pohang 37673, South Korea

[2] Pohang Univ Sci & Technol, Dept Chem, Pohang 37673, South Korea

[3] Pohang Univ Sci & Technol, Div Adv Mat Sci, Pohang 37673, South Korea

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 01期

关键词：

carbenes; iminoxyl radicals; nucleophilic addition; structure determination; X-ray diffraction; NITROUS-OXIDE; MECHANISM; DISPROPORTIONATION; REACTIVITY; TEMPO;

D O I：

10.1002/anie.201710530

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-heterocyclic carbene (NHC) nitric oxide (NHCNO) radicals, which can be regarded as iminoxyl radicals stabilized by NHCs, were found to react with a series of silyl and alkyl triflates to generate the corresponding oxime ether radical cations. The structures of the resulting oxime ether radical cations were determined by X-ray crystallography, along with EPR and computational analysis. In contrast, lutidinium triflate produced a 1:1 mixture of [NHCNO+][OTf-] and [NHCNHOH+][OTf-] upon the reaction with NHCNO. This study adds an important example of stable singlet carbenes for stabilizing main-group radicals because of their pi-conjugating effect, the synthesis and structures of which have not been reported previously.

引用

页码：262 / 265

页数：4