Ground state oxygen in synthesis of cyclic peroxides. Part 1: Benzo fused ketals

Junwon Kim, Hong Bin Li, Andrew S. Rosenthal, Dongpei Sang, Theresa A. Shapiro, Mario D. Bachi, Gary H. Posner

Research output: Contribution to journalArticlepeer-review

Abstract

A thiol-olefin-cooxygenation (TOCO) radical chain reaction involving ground state molecular oxygen converts 2′-isopropenyl acetophenones directly into cyclic peroxy hemiketal products with three new bonds. Starting with 4-t-butylbenzenethiol, this TOCO process proceeds reproducibly on gram scale in 86% yield. Hemiketal→ketal and sulfide→sulfone transformations finally provide a series of sulfonyl cyclic peroxy ketals. The in vitro antimalarial activities of some of these structurally simple benzo-fused cyclic peroxides are reported.

Original languageEnglish (US)
Pages (from-to)4120-4127
Number of pages8
JournalTetrahedron
Volume62
Issue number17
DOIs
StatePublished - Apr 24 2006

Keywords

  • Endoperoxides
  • Malaria
  • Molecular oxygen
  • Radical oxygenation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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