Structure and Stereodynamics of N,N-Bis(silyloxy)enamines
Journal of the American Chemical Society2002Vol. 124(38), pp. 11358–11367
Citations Over TimeTop 22% of 2002 papers
Alexander A. Tishkov, Alexander D. Dilman, V. I. Faustov, A.A. Birukov, K.S. Lysenko, Paul A. Belyakov, Sema L. Ioffe, Yury A. Strelenko, M. Yu. Antipin
Abstract
The structure and stereodynamics of N,N-bis(silyloxy)enamines (1), a new class of enamines with extraordinary reactivity, have been simulated by the DFT PBE/TZP method. The computed pattern of dynamic behavior and structural peculiarities of 1 was shown to reflect adequately the results of the studies by a series of physical methods including X-ray analysis and dynamic NMR and UV spectroscopies, which provided evidence of a rather low barrier for rotation around the C,N single bond, a negligible contribution of the n-pi-conjugation, a high barrier of inversion, and high pyramidality of the nitrogen atom.
Related Papers
- → Configurational stability of pyramidal nitrogen in spiro-oxaziridines(1973)36 cited
- → Study of Polyfunctional Diazo Compounds Reactivity in Heterocyclization by the Method of Intramolecular Competitive Reactions(1993)25 cited
- → Nitrogen Stereodynamics and Complexation Phenomena as Key Factors in the Deprotonative Dynamic Resolution of Alkylideneaziridines: A Spectroscopic and Computational Study(2015)12 cited
- → Conformational equilibria and nitrogen inversion in tetrahydro-1,2,5-oxadiazines(1979)10 cited
- → Use of the method of atom-atom potentials to analyze the structure of nitrogen-containing compounds(1978)