Structure and stereodynamics of N,N-bis(silyloxy)enamines.
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.
Tishkov
Alexander A
AA
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky Prosp. 47, Moscow, Russian Federation. tishkov@cacr.ioc.ac.ru
Dilman
Alexander D
AD
Faustov
Valery I
VI
Birukov
Arsenij A
AA
Lysenko
Konstantin S
KS
Belyakov
Paul A
PA
Ioffe
Sema L
SL
Strelenko
Yury A
YA
Antipin
Michael Yu
MY