123529-68-0Relevant articles and documents
The reaction of N-trimethylsilyl-amides and lactams with dimethyl(chloromethyl)chlorosilane. Kinetically controlled formation of (N-Si) chelate intermediates, O-imidates and their reaarangement to final (O-Si) chelate N-amides...
Kalikhman, I. D.,Albanov, A. I.,Bannikova, O. B.,Belusova, L. I.,Voronkov, M. G.,et al.
, p. 147 - 156 (1989)
The multistage character of the reaction of dimethyl(chloromethyl)chlorosilane (I) with N-trimethylsilyl-amides and -lactams (II) was shown by NMR monitoring.Interaction of the reactants starts with transsilylation, leading to Me3SiCl and the corresponding N-amide or-lactam (III).The second stage, intramolecular (dimethylchlorosilyl)methylation of unstable III, proceeds in two directions.A kinetically controlled transformation of III affords previously unknown O-(dimethylchlorosilyl)methylated intermediates, O-imidates (IV) containing a hypervalent Cl-Si-N bond.The already known products (O-Si) chelate N-(dimethylchlorosilyl)methyl>amides (V), arise from the reaction carried out under thermodinamic control.The same compounds are also formed via the Chapman rearrangement of the intermediates (IV).
