86657-60-5Relevant academic research and scientific papers
Diels-Alder Adducts of 1,7-Dehydroquadricyclane
Baumgaertel, Otto,Harnisch, Joachim,Szeimies, Guenter,Meerssche, Maurice Van,Germain, Gabriel,Declercq, Jean-Paul
, p. 2205 - 2218 (2007/10/02)
The reaction of bulky lithium amides and 1-chloroquadricyclane in the presence of anthracene, 9-methoxyanthracene, 2,5-dimethylfuran, furan, and 1,2,3-trimethylisoindole afforded the corresponding Diels-Alder adducts of 1,7-dehydroquadricyclane 4a, 4b, 8a, 10 and 17 in satisfactory to good yields.The structure of 4a has been established by x-ray analysis.Attempts to isomerize the quadricyclane parts of the adducts to the corresponding norbornadiene units led only to polymeric material.Thiophenol selectively cleaved the central propellane bond of 4a to give the thioether 28a.Dimethyl acetylenedicarboxylate and diethyl azodicarboxylate reacted with the quadricyclane system of 17 leading to the bridgehead olefins 24 and 25.
