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

Adima Augustin | Zendy; Bied Catherine | Zendy; Moreau Joël J. E | Zendy; Wong Chi Man Michel | Zendy

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

Author(s) -

Adima Augustin,

Bied Catherine,

Moreau Joël J. E,

Wong Chi Man Michel

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400079

Subject(s) - chemistry , cleavage (geology) , cyclohexane , hydrolysis , methylation , silsesquioxane , primary (astronomy) , bond cleavage , silica gel , organic chemistry , medicinal chemistry , polymer chemistry , catalysis , biochemistry , physics , geotechnical engineering , astronomy , fracture (geology) , engineering , gene , polymer

The reaction of chloromethyltriethoxysilane with (1 R ,2 R )‐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 (1 R ,2 R )‐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)

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