Accession Number:

ADA058349

Title:

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

Descriptive Note:

Technical rept.,

Corporate Author:

ILLINOIS UNIV AT URBANA-CHAMPAIGN DEPT OF CHEMISTRY

Personal Author(s):

Report Date:

1978-08-22

Pagination or Media Count:

24.0

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

Subject Categories:

  • Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE