On the Reaction of Alkylsilicon Fluorides with Primary Amines.

Tansjö, Lewi; Olsson, Ann; Elvidge, J. A.; Burton, J. S.; Stevens, Roger

doi:10.3891/acta.chem.scand.18-0456

Cited by 16 publications

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“…We next targeted the direct introduction of two amino groups to the double-decker silsesquioxane using our synthetic method, which should be feasible on the basis of previous reports that showed dialkyldifluorosilane and trialkylmonofluorosilane do not react with primary amines under completely dry conditions. 32 When 3-aminopropylmethyldiethoxysilane was treated with excess BF 3 •Et 2 O under solvent-free conditions, a difluorosilane bearing a BF 3 -complexed amino propyl group (1c) was obtained in high yield after distillation. The 19 F NMR spectrum showed a typical 1:1:1:1 quartet signal due to the B−F coupling at −151.9 ppm for the BF 3 moiety and a singlet signal at −136.1 ppm from the SiF 2 group.…”

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“…Although diamino-functionalized and well-defined silsesquioxanes have been previously reported, − multiple steps are required to obtain the desired product, since amino groups cannot coexist with chlorosilane because of the possible formation of aminosilane. We next targeted the direct introduction of two amino groups to the double-decker silsesquioxane using our synthetic method, which should be feasible on the basis of previous reports that showed dialkyldifluorosilane and trialkylmonofluorosilane do not react with primary amines under completely dry conditions . When 3-aminopropylmethyldiethoxysilane was treated with excess BF 3 ·Et 2 O under solvent-free conditions, a difluorosilane bearing a BF 3 -complexed amino propyl group ( 1c ) was obtained in high yield after distillation.…”

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Synthesis of Double-Decker Silsesquioxanes from Substituted Difluorosilane

et al. 2019

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A novel synthetic method for the construction of a double-decker silsesquioxane from fluorosilanes was developed. Phenyl-substituted double-decker silsesquioxane was prepared under mild conditions by coupling difluorodiphenylsilane and a tetrasiloxanolate precursor. A similar reaction was performed using difluorovinylsilane, and a divinyl double-decker silsesquioxane was obtained. The one-step reaction of a functional difluorosilane containing an aminopropyl group afforded a novel double-decker silsesquioxane with two amino groups complexed with BF3, which can react with carboxylic acid anhydrides to afford an amide product. This synthetic method using difluorosilane is tolerant of a wide range of functional groups and is applicable to the synthesis of polycyclic silsesquioxanes bearing amino groups, which are difficult to directly obtain from dichlorosilane.

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confidence: 99%