Ring-Expansion Reaction of Oximes with Aluminum Reductants

doi:10.3390/molecules17067348

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

Article

Ring-Expansion Reaction of Oximes with Aluminum Reductants

Hidetsura Cho^1,2,* , Yusuke Iwama², Nakako Mitsuhashi², Kenji Sugimoto², Kentaro Okano² and Hidetoshi Tokuyama^2,*

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; 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(O^tBu)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)

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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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