Six‐Membered Cyclic Nitroso Acetals: Synthesis and Studies of the Nitrogen Inversion Process of N‐Silyloxy‐3,6‐dihydro‐2H‐1,2‐oxazines

Six‐Membered Cyclic Nitroso Acetals: Synthesis and Studies of the Nitrogen Inversion Process of N‐Silyloxy‐3,6‐dihydro‐2H‐1,2‐oxazines Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2016, Volume: 2016, Number: 33, Pages: 5569-5578 Pages count : 10 DOI: 10.1002/ejoc.201600952

Authors

Shved Alexander S. ^1,2 , Tabolin Andrey A. ¹ , Novikov Roman A. ³ , Nelyubina Yulia V. ⁴ , Timofeev Vladimir P. ³ , Ioffe Sema L. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation
2	Higher Chemical College, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, 125047 Moscow, Russian Federation
3	V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov str. 32, 119991 Moscow, Russian Federation
4	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, 119991 Moscow, Russian Federation

Silyl nitronates undergo rhodium-catalyzed formal [3+3]-cycloaddition with enol diazoacetates to form N-silyloxy-3,6-dihydro-2H-1,2-oxazines. The scope of the reaction and the extent of the major side process were evaluated. A mechanistic scheme was proposed. The nitrogen inversion barrier in the obtained nitroso acetals was estimated based on both quantum calculations and kinetic measurements.

Shved A.S. , Tabolin A.A. , Novikov R.A. , Nelyubina Y.V. , Timofeev V.P. , Ioffe S.L.
Six‐Membered Cyclic Nitroso Acetals: Synthesis and Studies of the Nitrogen Inversion Process of N‐Silyloxy‐3,6‐dihydro‐2H‐1,2‐oxazines
European Journal of Organic Chemistry. 2016. V.2016. N33. P.5569-5578. DOI: 10.1002/ejoc.201600952 WOS Scopus OpenAlex

≡ Web of science:	WOS:000388493800015
≡ Scopus:	2-s2.0-85027920213
≡ OpenAlex:	W2546185350