Generation of singlet oxygen (O-1(2)) from hydrogen peroxide decomposition by in situ generated hypervalent iodoarene reagents

KALAY E., KILIÇ H., Catir M., ÇAKICI M., KAZAZ C.

PURE AND APPLIED CHEMISTRY, vol.86, no.6, pp.945-952, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 86 Issue: 6
  • Publication Date: 2014
  • Doi Number: 10.1515/pac-2013-0812
  • Journal Name: PURE AND APPLIED CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.945-952
  • Keywords: catalysis, homogeneous catalysis, hypervalent compounds, IUPAC Congress-44, Chemical Synthesis, oxidation, oxygen, oxygenation, peroxides, radicals, singlet oxygen, TERT-BUTYL HYDROPEROXIDE, MAIN-GROUP ELEMENTS, TRANSITION-METALS, ALLYLIC ALCOHOLS, MULTIPLE BONDS, EPOXIDATION, OXIDATION, CHEMISTRY, DIASTEREOSELECTIVITY, STEREOCHEMISTRY
  • Ataturk University Affiliated: Yes

Abstract

A novel method for the production of singlet oxygen from H2O2 was developed. A combination of iodoarene (ArI), methyltrioxorhenium (MTO), and H2O2 in the presence of pyridine as the co-catalyst efficiently produced singlet molecular oxygen (O-1(2)) under biphasic conditions. The existence of O-1(2) was demonstrated by trapping experiments with aromatic dienes, 1,3-cyclodienes, and alkenes. The mechanism of O-1(2) production from the iodoarene/MTO/35 % H2O2 system and the reaction scope was also discussed.