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- Title
Six-Membered Cyclic Nitroso Acetals: Synthesis and Studies of the Nitrogen Inversion Process of N-Silyloxy-3,6-dihydro-2 H-1,2-oxazines.
- Authors
Shved, Alexander S.; Tabolin, Andrey A.; Novikov, Roman A.; Nelyubina, Yulia V.; Timofeev, Vladimir P.; Ioffe, Sema L.
- Abstract
Silyl nitronates undergo rhodium-catalyzed formal [3+3]-cycloaddition with enol diazoacetates to form N-silyloxy-3,6-dihydro-2 H-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.
- Subjects
RING formation (Chemistry); NITROSO compounds; ACETAL resins; OXAZINES; HETEROCYCLIC compounds
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 33, p5569
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600952