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Unexpected formation of 9,10-dibenzoylphenanthrene
Marchand, Alan P. Srinivas, Gadthula Watson, William H.
Marchand, Alan P.
Srinivas, Gadthula
Watson, William H.
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Michigan Publishing, University of Michigan Library
Date
2002-11-21
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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.
Contents
Subject
Phencyclone
oxidative degradation
Diels-Alder reaction
X-ray crystal structure
oxidative degradation
Diels-Alder reaction
X-ray crystal structure
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Chemistry and Biochemistry