Abstract
Tetrahloro- o-benzoquinone ( 1) reacts with 6,6-diphenyl- and 6,6-bis ( p-methoxyphenyl)fulvene resp. ( 2a, b) forming [π4 + π2]-cycloadducts of the dihydrobenzodioxin type ( 4a, b); besides 6,6-dimethyl- and 6,6-pentamethylenefulvene ( 2c, d) yield dimeric 1:1-adducts ( 7c, d; 8c, d), which originated from primarily formed [π4 + π6]-cycloadducts of the dihydrobenzo [b]cyclopenta [e] [1·4]dioxepin type ( 6c, d) through a Diels-Alder reaction. The structures of 7c, d and 8c have been clarified through X-ray crystallography. Some investigations concerning the mechanism are reported.
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