7249-39-0Relevant academic research and scientific papers
SOLVENT EFFECT AS THE RESULT OF FRONTIER MOLECULAR ORBITAL INTERACTION. V. DIELS-ALDER WITH HETERODIENOPHILES: A UNIFIED APPROACH TO THE SOLVENT EFFECT OF THE DIELS-ALDER REACTIONS.
Desimoni, G.,Faita, G.,Righetti, P. P.,Toma, L.
, p. 7951 - 7970 (1990)
The solvent effect of Diels-Alder (D.A.) reactions with heterodienophiles was measured in several solvents.The rate of the reaction between 2,3-dimethylbutadiene (DMB) and diethylazodicarboxylate increases with the increases in the Acceptor Number of the solvent which behaves as an electrophile.The rate of the reaction between DMB and p-bromonitrosobenzene shows a small solvent effect which correlates with the cohesive pressure (δH2) of the solvent.The rate of the reactions between DMB and tetrachloro- or tetrabromo-o-benzoquinones give an inverse linear relationship with D? basicity parameters, thus rate decreases with increases in the nucleophilic character of the solvent.These monoparametric correlations (alternatively obtained with electrophilic, nucleophilic or cohesive pressure parameters of the solvent) rationalize the solvent effect of D.A. reactions reported in the literature, which fit one of the above reported three classes.The same result is obtained if the Kamlet-Taft multiparametric equation is applied to the same set of reactions.The main contribution remains that outlined with the nonparametric approach and some secondary effects or some borderline cases are usefully focussed.
Copper(II)-catalyzed aerobic oxidation of hydrazides to Azo intermediates and their Diels-Alder versus ene trapping
Chaiyaveij, Duangduan,Whiting, Andrew
supporting information, (2021/12/01)
The oxidation of diethyl 1, 2-hydrazinedicarboxylate using a catalytic Cu(II)-oxazoline system occurs at RT in air, resulting in azo generation, which can then be trapped in situ via hetero-Diels-Alder (HDA) and competitive ene-reactions, with chemoselect
A facile and convenient synthesis of 1,2,3,6-tetrahydropyridazines using azodicarboxylates under lanthanum triflate catalysis
Curini, Massimo,Epifano, Francesco,Marcotullio, Maria Carla,Rosati, Ornelio
, p. 1599 - 1604 (2007/10/03)
The hetero-Diels-Alder reaction catalyzed by lanthanum triflate hydrate using diethyl azodicarboxylate as dienophile, yielding differently substituted 1,2,3,6-tetrahydropyridazines, is described.
