Ring-expansion reaction of oximes with aluminum reductants

Hidetsura Cho; Yusuke Iwama; Nakako Mitsuhashi; Kenji Sugimoto; Kentaro Okano; Hidetoshi Tokuyama

doi:10.3390/molecules17067348

Ring-expansion reaction of oximes with aluminum reductants

Molecules. 2012 Jun 14;17(6):7348-55. doi: 10.3390/molecules17067348.

Authors

Hidetsura Cho¹, Yusuke Iwama, Nakako Mitsuhashi, Kenji Sugimoto, Kentaro Okano, Hidetoshi Tokuyama

Affiliation

¹ Graduate School of Science, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan. hcho@mail.pharm.tohoku.ac.jp

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aluminum Compounds / chemistry*
Oximes / chemistry*
Reducing Agents / chemistry*

Substances

Aluminum Compounds
Oximes
Reducing Agents