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Inverse Electron Demand Diels−Alder Reactivity and Electrochemistry of New Tetrazine Derivatives
Author(s) -
Li Yuan,
Miomandre Fabien,
Clavier Gilles,
Galmiche Laurent,
AlainRizzo Valérie,
Audebert Pierre
Publication year - 2017
Publication title -
chemelectrochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.182
H-Index - 59
ISSN - 2196-0216
DOI - 10.1002/celc.201600498
Subject(s) - tetrazine , reactivity (psychology) , atomic orbital , substituent , molecular orbital , computational chemistry , chemistry , diels–alder reaction , electrochemistry , electron , organic chemistry , physics , molecule , quantum mechanics , catalysis , medicine , alternative medicine , electrode , pathology
New tetrazine derivatives were prepared and their electrochemical properties as well as their reactivity in the inverse demand Diels−Alder (DAinv) reaction were investigated. DFT calculations were performed to calculate the energy and electronic distribution in the frontier molecular orbitals. In particular, the reactivity of these tetrazine derivatives has been compared with that of the already known dichlorotetrazine. A comparison of the gathered data allows a rough correlation to be established between the reactivity and the electron‐withdrawing character of the substituent, but only a closer examination of the involved orbitals can enable an accurate prediction of the DAinv reactivity of the investigated compounds.