Facile Cleavage of Si−C Bonds during the Sol‐Gel Hydrolysis of Aminomethyltrialkoxysilanes − A New Method for the Methylation of Primary Amines

Abstract

AbstractThe 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)