Theoretical Studies on the Mechanism of the Formation of Cyclopentadienes and Dihydropyridazines
Özet
The synthesis of cyclopentadiene derivatives via the domino reaction of norbornadienes with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate, followed a retro-Diels-Alder reaction, was reported by Dalkilic few years ago (Tetrahedron 2015;71 : 1966). In some cases, the formation of an unexpected dihydropyridazine (DHP) was observed, and explained by a 1,3-hydrogen shift. A density functional theory study is herein reported giving insights into the proposed mechanisms with different substituents on norbornadiene. Based on the kinetic and thermodynamic data, the retro-Diels-Alder reaction is confirmed to explain the formation of cyclopentadienes plus pyridazines. The intramolecular 1,3-hydrogen shift mechanism was not sufficient to explain the exclusive formation of two DHPs. Thus, an alternative mechanism involving a stepwise tautomerisation is being reported for formation of DHPs.
Anahtar kelimeler
Atıf için künye
Hallooman, D., Rhyman, L., Dalkilic, E., Daştan, A., Elzagheid, M., Domingo, L. R., & Ramasami, P. (2021). Theoretical Studies on the Mechanism of the Formation of Cyclopentadienes and Dihydropyridazines. ChemistrySelect, 6(37), 9806–9813. https://doi.org/10.1002/slct.202102928
BibTeX
@article{hallooman2021-70676,
author = {Hallooman, Dhanashree and Rhyman, Lydia and Dalkilic, Erdin and Daştan, Arif and Elzagheid, Mohamed and Domingo, Luis R. and Ramasami, Ponnadurai},
title = {Theoretical Studies on the Mechanism of the Formation of Cyclopentadienes and Dihydropyridazines},
journal = {ChemistrySelect},
year = {2021},
volume = {6},
number = {37},
pages = {9806--9813},
issn = {2365-6549},
doi = {10.1002/slct.202102928},
url = {https://akademik.atauni.edu.tr/yayinlar/70676-theoretical-studies-on-the-mechanism-of-the-formation-of-cyclopentadienes-and}
}