Mechanistic Investigation of the Acenaphthenequinone Sensitized Bartlett Photoepoxidation of Olefins. Concomitant Oxidation of the Sensitizer.

Abstract

Photolysis of acenaphthenequinone in Ch2Cl2 solution continuously saturated with oxygen generates 1,8-naphthalic anhydride in 80% isolated yield. When an olefin is included in the reaction solution it is converted to a mixture of oxidized products consisting mainly of allylic hydroperoxide and epoxide. It is demonstrated that the quantum efficiency for quinone oxidation is independent of quinone and olefin concentration. A mechanism is suggested for which an initial reaction between excited quinone and oxygen results in covalent bond formation. Subsequent rearrangement of this intermediate accounts for the results observed. (Author)

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Document Details

Document Type
Technical Report
Publication Date
Aug 22, 1978
Accession Number
ADA058349

Entities

People

  • Gary Schuster
  • Ja-young Koo

Organizations

  • University of Illinois Urbana–Champaign

Tags

Communities of Interest

  • Energy and Power Technologies

DTIC Thesaurus Topics

  • Chemical Reactions
  • Chemical Synthesis
  • Chemistry
  • Cyclohexenes
  • Electron Transfer
  • Materials Science
  • Military Research
  • New York
  • Organic Chemistry
  • Oxidation
  • Oxides
  • Oxygen
  • Photolysis
  • Quantum Efficiency
  • Quantum Yields
  • Spectra
  • United States

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry

Technology Areas

  • Quantum Computing