US EPA

8437863 

Journal Article 

Addition of Silicon Hydrides to Olefinic Double Bonds. XII. Use of Aminosilicon Hydrides and Silazane Hydrides 

Dennis, WE; Speier, JL 

1970 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

35 

11 

3879-3884 

English 

10.1021/jo00836a065 

The addition of aminosilicon hydrides and silazane hydrides to olefins and to dimethylaminodimethylvinylsilane in the presence of chloroplatinic acid was studied. n-Butylaminodimethylsilane and hexene-1 formed 2-n- butyl-l-n-hexyl-l,l,3,3-tetramethyldisilazane which diminished as the reaction proceeded to form n-butylamino- hexyldimethylsilane. Dialkylaminodimethylsilanes and trisdimethyls minosilane reacted very little, if at all, with olefins. sym-Tetramethyldisilazane behaved much like sym-tetramethyldisiloxane in having similar reactivity and in forming sec-alkyl adducts from pentene-2. Dimethylaminodimethylsilane added to hexene-1 smoothly in the presence of sym-tetramethyldisilazane, but not in its absence. Methyl methacrylate, methyl acrylate, allyl chloride, methallyl chloride, or allyl acetate each gave complex mixtures of many products with sym-tetramethyldisilazane. Allylamine gave hydrogen. Trisdimethylsilylamine formed the dihexyl adduct, no tri- hexyl adduct, and products that indicated redistribution of methyl groups and hydrogen on the silicon atoms during the reaction. Poly-N-allylmethylsilazane reacted to form a polymer which degraded in methanol to form 2-(dimethoxymethylsilyl)propylamine.© 1970, American Chemical Society. All rights reserved.