Chemically Triggered C-ON Bond Homolysis of Alkoxyamines. Quaternization of the Alkyl Fragment

被引：48

作者：

Bremond, Paul ^{[1
]}

Koita, Abdoulaye ^{[1
]}

Marque, Sylvain R. A. ^{[1
]}

Pesce, Vincent ^{[1
]}

Roubaud, Valerie ^{[1
]}

Siri, Didier ^{[1
]}

机构：

[1] Univ Aix Marseille 1, CNRS, UMR 6264, Lab Chim Provence, F-13397 Marseille 20, France

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 01期

关键词：

LONG-RANGE POLAR; RADICAL POLYMERIZATION; MULTIPARAMETER ANALYSIS; SG1-BASED ALKOXYAMINES; RATE CONSTANTS; SERIES;

D O I：

10.1021/ol2031075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C-ON bond homolysis in alkoxyamine 2a can be chemically triggered by the protonation of the 4-pyridylalkyl fragment. The resulting 15-fold increase In k(d) (Chem. Commun. 2011, 47, 4291-4293) was investigated experimentally and theoretically by quaternization of the pyridyl moiety using methylating (MeOTs), acylating (AcCl), and benzylating (PhCH2Br) agents as well as by oxidation of the pyridyl moiety into N-oxide and by the formation of a dative bond with BH3 as a Lewis acid.

引用

页码：358 / 361

页数：4

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