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Molecules 2012, 17(6), 7348-7355; https://doi.org/10.3390/molecules17067348

Ring-Expansion Reaction of Oximes with Aluminum Reductants

1
Graduate School of Science, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan
2
Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan
*
Authors to whom correspondence should be addressed.
Received: 5 April 2012 / Revised: 4 June 2012 / Accepted: 7 June 2012 / Published: 14 June 2012
(This article belongs to the Special Issue Heterocycles)
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Abstract

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.
Keywords: aluminum reductant; dichloroaluminum hydride (AlHCl2); ring-expansion of oxime; rearrangement of oxime; cyclopentyl methyl ether (CPME) aluminum reductant; dichloroaluminum hydride (AlHCl2); ring-expansion of oxime; rearrangement of oxime; cyclopentyl methyl ether (CPME)
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Cho, H.; Iwama, Y.; Mitsuhashi, N.; Sugimoto, K.; Okano, K.; Tokuyama, H. Ring-Expansion Reaction of Oximes with Aluminum Reductants. Molecules 2012, 17, 7348-7355.

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