Unexpected formation of 9,10-dibenzoylphenanthreneShow simple item record
| dc.creator | Marchand, Alan P. | |
| dc.creator | Srinivas, Gadthula | |
| dc.creator | Watson, William H. | |
| dc.date.accessioned | 2019-07-12T16:02:28Z | |
| dc.date.available | 2019-07-12T16:02:28Z | |
| dc.date.issued | 2002-11-21 | |
| dc.identifier.uri | https://doi.org/10.3998/ark.5550190.0004.302 | |
| dc.identifier.uri | https://repository.tcu.edu/handle/116099117/26457 | |
| dc.identifier.uri | https://quod.lib.umich.edu/a/ark/5550190.0004.302/1 | |
| dc.description.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. | |
| dc.language.iso | en | en_US |
| dc.publisher | Michigan Publishing, University of Michigan Library | |
| dc.rights.uri | https://creativecommons.org/licenses/by-nc/3.0/ | |
| dc.source | Arkivoc | |
| dc.subject | Phencyclone | |
| dc.subject | oxidative degradation | |
| dc.subject | Diels-Alder reaction | |
| dc.subject | X-ray crystal structure | |
| dc.title | Unexpected formation of 9,10-dibenzoylphenanthrene | |
| dc.type | Article | |
| dc.rights.holder | Alan P. Marchand et al. | |
| dc.rights.license | CC BY-NC 3.0 | |
| local.college | College of Science and Engineering | |
| local.department | Chemistry and Biochemistry | |
| local.persons | Watson (CHEM) |
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