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Synthesis and Topochemistry of 2,5-Bisacrylate-Substituted 1,4-Benzoquinones

✍ Scribed by Hermann Irngartinger; Rüdiger Herpich

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
784 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis

The 2,5-bisacrylate-substituted 1,4-benzoquinone bisketal 7a was synthesized by electrochemical oxidation of the corresponding dimethoxybenzene 6. The methyl ester 7a was transesterified to the corresponding ethyl, n-propyl and isopropyl esters 7bϪ7d by Ti(OEt) 4 catalysis and to the corresponding n-butyl and benzyl esters 7eϪ7f by the Li alkoxides. The bisketals 7aϪ7f were hydrolyzed to the corresponding 2,5-bisacrylate-substituted 1,4-benzoquinones 1aϪ1f. The crystal structure of the ethyl ester 1b was determined by X-ray diffraction, which revealed short intermolecular contacts of 3.463 and 4.051 A ˚between vinyl groups and quinone double bonds, respectively, related by twofold symmetry. Be-

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