Structure and Stereodynamics of N,N-Bis(silyloxy)enamines

Structure and Stereodynamics of N,N-Bis(silyloxy)enamines Full article

Journal

Journal of the American Chemical Society
ISSN: 0002-7863 , E-ISSN: 1520-5126

Output data

Year: 2002, Volume: 124, Number: 38, Pages: 11358-11367 Pages count : 10 DOI: 10.1021/ja026548i

Authors

Tishkov Alexander A. ^1,2 , Dilman Alexander D. ^1,2 , Faustov Valery I. ^1,2 , Birukov Arsenij A. ^1,2 , Lysenko Konstantin S. ^1,2 , Belyakov Paul A. ^1,2 , Ioffe Sema L. ^1,2 , Strelenko Yury A. ^1,2 , Antipin Michael Yu. ^1,2

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky Prosp. 47, Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Vavilova str. 28, Moscow, Russian Federation

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−π-conjugation, a high barrier of inversion, and high pyramidality of the nitrogen atom.

Tishkov A.A. , Dilman A.D. , Faustov V.I. , Birukov A.A. , Lysenko K.S. , Belyakov P.A. , Ioffe S.L. , Strelenko Y.A. , Antipin M.Y.
Structure and Stereodynamics of N,N-Bis(silyloxy)enamines
Journal of the American Chemical Society. 2002. V.124. N38. P.11358-11367. DOI: 10.1021/ja026548i WOS Scopus OpenAlex

Web of science:	WOS:000178104600042
Scopus:	2-s2.0-0037174451
OpenAlex:	W1985922629

DB	Citing
OpenAlex	29
Scopus	26
Web of science	25