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Structure and stereodynamics of N,N-bis(silyloxy)enamines
Alexander A Tishkov1, Alexander D Dilman, Valery I Faustov
1N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky Prosp. 47, Moscow, Russian Federation. tishkov@cacr.ioc.ac.ru
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.
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