Evidence for the concerted mechanism of the Diels-Alder reaction of butadiene with ethylene

1986 ◽  
Vol 108 (3) ◽  
pp. 554-556 ◽  
Author(s):  
K. N. Houk ◽  
Yi Tsong. Lin ◽  
Frank K. Brown
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Concerted Mechanism ◽  
Diels Alder Reaction

scholarly journals Theoretical Study on Synthesis of Sylvestrene by Cyclodimerization of Isoprene: Asynchronous Concerted Mechanism of Diels-Alder Reaction

2014 ◽  
Vol 26 (4) ◽  
pp. 1019-1026
Author(s):  
Chuan-Ming Wang ◽  
Yi-Lei Chen ◽  
Zhi-Hua Liu ◽  
Yong-Kuan Chen ◽  
Jing-Mei Han ◽  
...  
Keyword(s):  
Theoretical Study ◽  
Alder Reaction ◽  
Diels Alder ◽  
Concerted Mechanism ◽  
Diels Alder Reaction

A theoretical study on the hetero-Diels–Alder reaction of phosphorous substituted diaza- and oxaza-alkenes with olefins derivatives

RSC Advances ◽  
2016 ◽  
Vol 6 (92) ◽  
pp. 89440-89449 ◽  
Author(s):  
M. Haghdadi ◽  
A. Abaszade ◽  
L. Abadian ◽  
N. Nab ◽  
H. Ghasemnejad Bosra
Keyword(s):  
Theoretical Study ◽  
Transition States ◽  
Alder Reaction ◽  
Diels Alder ◽  
Dft Studies ◽  
Concerted Mechanism ◽  
Diels Alder Reaction

DFT studies indicated that a hetero-Diels–Alder reaction of 4-phosphinyl and 4-phosphonyl-1,2-diaza- and 1,2-oxaza-1,3-butadienes with some olefins take place via an asynchronous concerted mechanism through endo or exo transition states.

scholarly journals Theoretical study on the Diels-Alder reaction of bromo-substituted 2H-pyrane-2-ones and some substituent vinyls

2015 ◽  
Vol 80 (9) ◽  
pp. 1139-1148
Author(s):  
Mina Haghdadi ◽  
Hamed Amani ◽  
Nasim Nab
Keyword(s):  
Density Functional ◽  
Theoretical Study ◽  
Alder Reaction ◽  
Diels Alder ◽  
Free Energies ◽  
Functional Theory ◽  
Concerted Mechanism ◽  
Diels Alder Reaction ◽  
Reaction Channels ◽  
Orbital Analysis

A DFT study of the reactivity, regio- and stereoselectivity of Diels-Alder reaction between 3-bromo, 5-bromo, and 3,5-dibromo-2(H)-pyran-2-ones and some weakly activated and unactivated alkenes has been carried out using density functional theory (DFT). Four possible reaction channels, which are related to the formation of meta- and para- and endo- and exo-cycloadducts have been explored and characterized. The energy and natural bond orbital analysis shows that the meta-regioselectivity on the exo pathway is preferred and follows an asynchronous concerted mechanism with a polar nature in all Diels-Alder cycloadditions. Moreover, the activation free energies of Diels-Alder cycloadditions of 3,5-dibromo-2(H)-pyran-2one are lower than 3- bromo-2(H)-pyran-2one and 5-bromo-2(H)-pyran-2one, which are in line with experimental observation. DFT-based reactivity indices clearly predict the regiochemistry of the isolated cycloadducts.

The Diels-Alder Reaction of 2-Ethenyl-1,4-Benzodioxin: A New and Simple Synthesis of Bisaryl Ethers

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Simple Synthesis ◽  
Diels Alder Reaction

The intermolecular anthracene-transfer in a regiospecific antipodal C60 difunctionalization

2020 ◽  
Author(s):  
Radu Talmazan ◽  
Klaus R. Liedl ◽  
Bernhard Kräutler ◽  
Maren Podewitz
Keyword(s):  
Noncovalent Interactions ◽  
Interaction Model ◽  
Alder Reaction ◽  
Diels Alder ◽  
Stacking Interactions ◽  
Pi Stacking ◽  
Diels Alder Reaction ◽  
Double Decker ◽  
Anthracene Molecule ◽  
New Strategies

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>

Natural Products Biosynthesis Involving a Putative Diels-Alder Reaction

2016 ◽  
Vol 20 (22) ◽  
pp. 2421-2442 ◽  
Author(s):  
Kévin Cottet ◽  
Maria Kolympadi ◽  
Dean Markovic ◽  
Marie-Christine Lallemand
Keyword(s):  
Natural Products ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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