Photooxidation of N,N′-Diacylindigo Dyes
Document Type
Article
Publication Date
12-1-1994
Abstract
Irradiation of N,N′-diacylindigo dyes in the presence of oxygen resulted in an unusual oxygen insertion/acyl transfer reaction. While this process occurred over many weeks at room temperature, at 100° C it was complete in a few hours. In some cases the yield of photooxidized product was virtually quantitative. The product structures were proved by spectroscopic methods and in one example by X-ray analysis. A series of mechanistic experiments led to the conclusion that at least the oxygen insertion part of the photooxidation process proceeded via a radical mechanism. The evidence included the following observations: (1) When the photooxidation was conducted in toluene, large amounts of benzyl hydroperoxide were produced; (2) the photooxidation could be achieved in the dark with a radical initiator; (3) attempts to generate the photooxidized product using singlet oxygen chemistry failed. The postulated radical mechanism is described. © 1994, American Chemical Society. All rights reserved.
Journal Title
Journal of Organic Chemistry
Volume
59
Issue
26
First Page
8011
Last Page
8014
DOI
https://doi.org/10.1021/jo00105a015
First Department
Chemistry and Biochemistry
Recommended Citation
Smith, Bradley D.; Alonso, David E.; Bien, Jeffrey T.; Metzler, Elise C.; Shang, Maoyu; and Roosenberg, John M. II, "Photooxidation of N,N′-Diacylindigo Dyes" (1994). Faculty Publications. 2562.
https://digitalcommons.andrews.edu/pubs/2562