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

Ring-Expansion Reaction of Oximes with Aluminum Reductants

1,2,* , 2, 2, 2, 2 and 2,*
Received: 5 April 2012; in revised form: 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)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Cho H, Iwama Y, Mitsuhashi N, Sugimoto K, Okano K, Tokuyama H. Ring-Expansion Reaction of Oximes with Aluminum Reductants. Molecules. 2012; 17(6):7348-7355.

Chicago/Turabian Style

Cho, Hidetsura; Iwama, Yusuke; Mitsuhashi, Nakako; Sugimoto, Kenji; Okano, Kentaro; Tokuyama, Hidetoshi. 2012. "Ring-Expansion Reaction of Oximes with Aluminum Reductants." Molecules 17, no. 6: 7348-7355.


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