An in-depth look at the effect of Lewis acid catalysts on Diels–Alder cycloadditions in ionic liquids

Tetrahedron ◽  
2005 ◽  
Vol 61 (30) ◽  
pp. 7105-7111 ◽  
Author(s):  
Guadalupe Silvero ◽  
María José Arévalo ◽  
José Luis Bravo ◽  
Martín Ávalos ◽  
José Luis Jiménez ◽  
...  
ChemInform ◽  
2005 ◽  
Vol 36 (45) ◽  
Author(s):  
Guadalupe Silvero ◽  
Maria Jose Arevalo ◽  
Jose Luis Bravo ◽  
Martin Avalos ◽  
Jose Luis Jimenez ◽  
...  

1975 ◽  
Vol 53 (4) ◽  
pp. 616-618 ◽  
Author(s):  
Žarko Stojanac ◽  
Robert A. Dickinson ◽  
Nada Stojanac ◽  
Ronald J. Woznow ◽  
Zdenek Valenta

Lewis acid catalysts cause an orientation reversal in the Diels–Alder additions of 2,6-di-methyl-1,4-quinone (1) and toluquinone (12) to 1-substituted 1,3-butadienes and to 1,2- and 1,3-dialkyl dienes. These results are explained by the preferential formation of one reactive quinone–Lewis acid salt.


Catalysts ◽  
2019 ◽  
Vol 9 (6) ◽  
pp. 534 ◽  
Author(s):  
Roberto Calmanti ◽  
Emanuele Amadio ◽  
Alvise Perosa ◽  
Maurizio Selva

The reactivity of glycerol with trimethyl orthoformate is here described with an emphasis on developing a reliable synthetic approach for glycerol valorization. The glycerol based orthoester 4-(dimethoxymethoxy)methyl)-2-methoxy-1,3-dioxolane (3) was synthesized, under catalytic as well as catalyst-free conditions, by taking advantage of the thermodynamically controlled equilibrium between intermediates. Both Brønsted and Lewis acid catalysts accelerated the attainment of such an equilibrium, particularly Brønsted acidic ionic liquids BSMImHSO4 and BSMImBr were the most effective compounds for this reaction. The kinetic profiles allowed the proposal of a mechanism that accounts for the selectivity of the reaction.


2000 ◽  
Vol 196 (1) ◽  
pp. 86-94 ◽  
Author(s):  
C. DeCastro ◽  
E. Sauvage ◽  
M.H. Valkenberg ◽  
W.F. Hölderich

1989 ◽  
Vol 30 (11) ◽  
pp. 1357-1360 ◽  
Author(s):  
T. Ross Kelly ◽  
Sanat K. Maity ◽  
Premji Meghani ◽  
Nizal S. Chandrakumar

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