Abstract
The first representatives of (O-Si) chelated N-[(trifluorosilyl)methyl]anilides were synthesized. N-(Trimethylsilyl)acetanilide reacts with bifunctional silane ClCH2SiF3 with the formation of N-[(trifluorosilyl)methyl]acetanilide as the only product. N-[(Trifluorosilyl)methyl]benzanilide was obtained by similar alkylation of benzanilide with ClCH2SiF3 in the presence of DBU as a base. The structure of the products was proved by NMR and X-ray analysis. The energy of the C=O→Si dative bond in the obtained anilides was estimated by the QTAIM analysis. The calculated values lie near 40 kcal/mol, which is larger than in previously studied N-[difluoro(methyl)silyl]methylcarboxamides (14–30 kcal/mol).
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