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

13 Citations (Scopus)

Abstract

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
JournalMolecules
Volume17
Issue number6
DOIs
Publication statusPublished - 2012 Jun

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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