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

Ring-Expansion Reaction of Oximes with Aluminum Reductants

1,2,* email, 2, 2, 2, 2 and 2,* email
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)
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.
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)
PDF Full-text Download PDF Full-Text [198 KB, uploaded 18 June 2014 19:49 CEST]

Export to BibTeX |
EndNote


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.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert