Ring-expansion reaction of oximes with aluminum reductants

The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl2, AlH3 (alane), LiAlH4, LiAlH(OtBu)3, and (MeOCH2CH2O)2AlH2Na (Red-Al) were examined. Among reductants, AlHCl2 (LiAlH4:AlCl3 = 1:3) in cyclopentyl methyl ether (CPME) has been found...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2012-06, Vol.17 (6), p.7348-7355
Hauptverfasser:	Cho, Hidetsura, Iwama, Yusuke, Mitsuhashi, Nakako, Sugimoto, Kenji, Okano, Kentaro, Tokuyama, Hidetoshi
Format:	Artikel
Sprache:	eng
Schlagworte:	Aluminum Aluminum Compounds - chemistry aluminum reductant cyclopentyl methyl ether (CPME) dichloroaluminum hydride (AlHCl 2 ) Oximes - chemistry Reagents rearrangement of oxime Reducing Agents - chemistry ring-expansion of oxime Solvents
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Beschreibung
Zusammenfassung:	The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl2, AlH3 (alane), LiAlH4, LiAlH(OtBu)3, and (MeOCH2CH2O)2AlH2Na (Red-Al) were examined. Among reductants, AlHCl2 (LiAlH4:AlCl3 = 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.
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules17067348