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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 5
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Original Articles

Synthesis of Bicyclo[4.2.0]Octa-3,7-Diene-2,5-Diones

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Pages 337-341 | Received 07 Aug 1973, Published online: 05 Dec 2006
 

Abstract

The bicyclo[4.2.0]octa-3,7-diene-2,5-diones (1) are of interest in that they are valence isomers of 1,4-cyclooctatetraenoquinones. The most obvious route for the formation of such compounds is the [2+2] photoaddition of alkynes to p-benzoquinones. Such a reaction has been observed in the case of 1,4-naphthoquinones. With p-benzoquinones, however, it has been observed in the case of 2-methoxy-p-benzoquinone (2a) alone, while p-benzoquinone (2b) and chloranil (2c) give products derived from addition of acetylenes to a carbonyl rather than an ethylenic bond; 3,4 such products also accompany the products from 1,4-naphthoquinones referred to above.1,3

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