1533410-35-3Relevant academic research and scientific papers
Transfer reagents 4: Retro-Diels-alder routes to 3,6-Di(2-pyridyl) pyridazinonorbornadiene, a test bed for the relative dienofugacity of isobenzofuran, isoindole, and anthracene
Margeti?, Davor,Butler, Douglas N.,Warrener, Ronald N.
, p. 2609 - 2613 (2013)
Norbornadiene cycloadducts reacted with 3,6-di(2-pyridyl)-s-tetrazine to produce pyridazines (diene-protected alkenes), following dehydrogenation (by DDQ) of the intermediate dihydropyridazines. The title 3,6-di(2-pyridyl)- pyridazinonorbornadiene was produced under flash vacuum pyrolysis conditions by ejection of anthracene (590? °C), isobenzofuran (630°C) or isoindole (580°C) from the corresponding pyridazines, establishing the following dienofugacity order: isoindole > anthracene > isobenzofuran. Calculations of the respective retro-Diels-alder activation energies at the B3LYP/6-31G* level of theory correctly predicted the experimentally found isobenzofuran > anthracene > isoindole order. Cavity bis-3,6-di(2-pyridyl) -pyridazine (dppn) and chevron-shaped bis-dppn ligands were prepared from the title compound by coupling at the norbornene π-bond.
