Ring-Expansion Reaction of Oximes with Aluminum Reductants

The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl(2), AlH(3) (alane), LiAlH(4), LiAlH(O(t)Bu)(3), and (MeOCH(2)CH(2)O)(2)AlH(2)Na (Red-Al) were examined. Among reductants, AlHCl(2) (LiAlH(4):AlCl(3) = 1:3) in cyclopentyl methyl eth...

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Detalles Bibliográficos
Autores principales: Cho, Hidetsura, Iwama, Yusuke, Mitsuhashi, Nakako, Sugimoto, Kenji, Okano, Kentaro, Tokuyama, Hidetoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268446/
https://www.ncbi.nlm.nih.gov/pubmed/22699568
http://dx.doi.org/10.3390/molecules17067348
Descripción
Sumario:The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl(2), AlH(3) (alane), LiAlH(4), LiAlH(O(t)Bu)(3), and (MeOCH(2)CH(2)O)(2)AlH(2)Na (Red-Al) were examined. Among reductants, AlHCl(2) (LiAlH(4):AlCl(3) = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.

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