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Bisadducts from the Diels-Alder Trapping of Bis(o-Xylenols) Photochemically Generated from 2,5-Dibenzoyl-p-xylenePhotolysis of 2,5-dibenzoyl-p-xylene produces two discrete o-xylenols which undergo Diels-Alder cycloadditions with standard dienophiles, such as methyl acrylate, to produce 1,5-dihydroxy-1,5-diphenyl-l,2,3,4,5,6,7,8-octahydroanthracenes, 2a, in good yield (greater than 80%). The anti bisadduct crystallizes into hydrogen bonded stacks. Conversion of both syn- and anti-bisadducts to the corresponding anthracenes was achieved through the use of standard dehydration and aromatization chemistry.
Document ID
20030112746
Acquisition Source
Glenn Research Center
Document Type
Preprint (Draft being sent to journal)
Authors
Meador, Michael A.
(NASA Glenn Research Center Cleveland, OH, United States)
Kinder, James D.
(NASA Glenn Research Center Cleveland, OH, United States)
Kirby, James P.
(NASA Glenn Research Center Cleveland, OH, United States)
Date Acquired
August 21, 2013
Publication Date
January 1, 2003
Subject Category
Inorganic, Organic And Physical Chemistry
Distribution Limits
Public
Copyright
Work of the US Gov. Public Use Permitted.
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