Ring-expansion reaction of oximes with aluminum reductants

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

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)


The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl 2, AlH 3 (alane), LiAlH 4, LiAlH(OtBu) 3, and (MeOCH 2CH 2O) 2AlH 2Na (Red-Al) were examined. Among reductants, AlHCl 2 (LiAlH 4:AlCl 3 = 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.

Original languageEnglish
Pages (from-to)7348-7355
Number of pages8
Issue number6
Publication statusPublished - 2012 Jun


  • Aluminum reductant
  • Cyclopentyl methyl ether (CPME)
  • Dichloroaluminum hydride (AlHCl )
  • Rearrangement of oxime
  • Ring-expansion of oxime


Dive into the research topics of 'Ring-expansion reaction of oximes with aluminum reductants'. Together they form a unique fingerprint.

Cite this