N,N-Bis(halomethyldimethylsilyl)acetamides and their reactions

Add time:08/27/2019    Source:sciencedirect.com

N,N-Bis(halomethyldimethydimethylsilyl)acetamides, MeCON(SiMe2CH2X)2, (X = Cl, Br) were prepared by transsilylation of N,O-bis(trimethylsilyl)acetamide with halomethyldimethylchlorosilane. With water and methanol, instead of the expected SiN cleavage, nucleophilic substitution of halogen took place and the products were 1-acetyl-2,2,6,6-tetramethyldisilamorpholine and N,N-bismethoxymethyldimethylsilyl)acetamide respectively. These compounds were shown by IR and 1H NMR spectra to have the N,N-disilylacetamide structure. Thermodynamic, kinetic constants of hindered rotation around the CN bond in these compounds were determined from their temperature-variable 1H NMR spectra. The main products of thermolysis of the silylamides are α,ω-dichloropolydimethylsiloxanes and polydimethylcyclosiloxanes.

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