Synthesis of novel macrocyclic peroxides by bis(sym-collidine)iodine (I) hexafluorophosphate-mediated cyclization of unsaturated hydroperoxides and unsaturated alcohols

Toyonari Ito, Takahiro Tokuyasu, Araki Masuyama, Masatomo Nojima, Kevin J. McCullough

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

Bis(sym-collidine)iodine (I) hexafluorophosphate-mediated cyclization of unsaturated hydroperoxides, prepared by a variety of different methods, afforded the corresponding 10- to 20-membered macrocyclic peroxides having two or three peroxide units located within one ring in moderate yields. By analogy, cyclization of unsaturated alcohols having one or two peroxide bond in the chain afforded the corresponding cyclic ethers. The efficiency of the latter reactions were found to be a function of the structure of the alcohols. © 2003 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)525-536
Number of pages12
JournalTetrahedron
Volume59
Issue number4
DOIs
Publication statusPublished - 20 Jan 2003

Keywords

  • Iodonium ion-mediated cyclization
  • Macrocyclic peroxide
  • Unsaturated alcohol
  • Unsaturated hydroperoxide

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