Facile cleavage of Si-C bonds during the sol-gel hydrolysis of aminomethyltrialkoxysilanes - A new method for the methylation of primary amines

被引：17

作者：

Adima, A ^{[1
]}

Bied, C ^{[1
]}

Moreau, JLJE ^{[1
]}

Man, MWC ^{[1
]}

机构：

[1] Ecole Natl Super Chim Montpellier, CNRS, UMR 5076, Lab Chim Organomet Heterochim Mol & Macromol, F-34296 Montpellier 05, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 12期

关键词：

alkylation; amines; condensation; hydrolysis; sol-gel processes;

D O I：

10.1002/ejoc.200400079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of chloromethyltriethoxysilane with (1R,2R)-bis(methylamino)cyclohexane (1) afforded the corresponding bis-silylated compound 2. The sol-gel hydrolysis of 2 did not give the expected bridged silsesquioxane owing to quantitative Si-C-bond cleavage. Instead, silica and (1R,2R)-bis(dimethylamino)cyclohexane (3) were obtained. This reaction was exploited to propose a new route for the methylation of amines. Such methylation reaction of amines could be extended to other amines and provides a new method for the selective monomethylation of primary amines. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

引用

页码：2582 / 2588

页数：7

共 55 条

[51] Zwitterionic lambda Si-5-organofluorosilicates of the formula types F(4)SiCH(2)NMe(2)R and F(3)MeSiCH(2)NMe(2)R (R=H, Me) and related compounds: Synthesis, structure, and dynamic behavior [J].