Unexpected formation of 9,10-dibenzoylphenanthreneShow full item record
| Title | Unexpected formation of 9,10-dibenzoylphenanthrene |
|---|---|
| Author | Marchand, Alan P.; Srinivas, Gadthula; Watson, William H. |
| Date | 2002-11-21 |
| Abstract | When heated in the presence of atmospheric oxygen, either in diffuse room light or in the dark, phencyclone (1) undergoes autoxidation to afford 9,10-dibenzoylphenanthrene (3). The structure of 3 was elucidated via application of single crystal X-ray crystallographic techniques. Amechanism is suggested to account for the formation of 3 via (i) stepwise 1,4-addition of 3O2 to the 1,3-diene system in the cyclopentadiene moiety of 1 to form endoperoxide 5 followed by (ii) cheletropic extrusion of carbon monoxide from 5. The structure of 3 is described: P21/C, a =12.116(2), b = 9.6850(2), c = 16.839(3) Angstrom, beta = 100.331(3) degres. |
| Link | https://doi.org/10.3998/ark.5550190.0004.302
https://repository.tcu.edu/handle/116099117/26457 https://quod.lib.umich.edu/a/ark/5550190.0004.302/1 |
| Department | Chemistry and Biochemistry |
| Subject | Phencyclone
oxidative degradation Diels-Alder reaction X-ray crystal structure |
Files in this item
This item appears in the following Collection(s)
- Research Publications [1008]
Except where otherwise noted, this item's license is described as https://creativecommons.org/licenses/by-nc/3.0/