20452-56-6Relevant articles and documents
Acid-induced rearrangement reactions of reduced benzoquinone cyclopentadiene cycloadducts
Eipert, Martin,Maichle-Moessmer, Caecilia,Maier, Martin E.
, p. 8692 - 8695 (2002)
Several Diels-Alder adducts between benzoquinones and cyclopentadiene were reduced to the corresponding diols 7a-c and 11. Treatment of these diols with strong acid triggered a skeletal rearrangement reaction resulting in compounds 8a-c and 12 that contain a 4,8-methanoazulene substructure. In addition, a dyotropic-like rearrangement of the tetracyclic lactone 13 to the spirolactone 18 was observed. Five of the structures were supported by X-ray analysis.