Pericyclic Reactions in Biological Systems—Does Nature Know About the Diels—Alder Reaction?

1996 ◽  
Vol 35 (3) ◽  
pp. 289-291 ◽  
Author(s):  
Sabine Laschat
Keyword(s):  
Biological Systems ◽  
Alder Reaction ◽  
Diels Alder ◽  
Pericyclic Reactions ◽  
Diels Alder Reaction

scholarly journals Are There Only Fold Catastrophes in the Diels–Alder Reaction Between Ethylene and 1,3–Butadiene?

2021 ◽  
Author(s):  
Leandro Ayarde-Henriquez ◽  
Cristian Guerra ◽  
Mario Duque-Noreña ◽  
Elizabeth Rincón ◽  
Patricia Pérez ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Unexpected Finding ◽  
Pericyclic Reactions ◽  
Topological Characterization ◽  
State Variable ◽  
Diels Alder Reaction ◽  
Fold Type ◽  
The One

This work revisits the topological characterization of the Diels–Alder reaction between 1,3–butadiene and ethylene. In contrast to the currently accepted rationalization, we here provide strong evidence in support of a representation in terms of seven structural stability domains separated by a sequence of 10 elementary catastrophes, but all only of the fold type, i.e., C<sub>4</sub>H<sub>6</sub> + C<sub>2</sub>H<sub>4 </sub>: 1–7– [FF]F[F<sup>†</sup>F<sup>†</sup>][F<sup>†</sup>F<sup>†</sup>][FF]F<sup>†</sup>–0 : C<sub>6</sub>H<sub>10</sub>. Such an unexpected finding provides fundamental new insights opening simplifying perspectives concerning the rationalization of the CC bond formation in pericyclic reactions in terms of the simplest Thom’s elementary catastrophe, namely the one–(state) variable, one–(control) parameter function.

Pericyclic Reactions: The Diels-Alder Reaction

2002 ◽  
Author(s):  
Juan Bertran ◽  
Vicen�� Branchadell ◽  
Antonio Oliva ◽  
Mariona Sodupe
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Pericyclic Reactions ◽  
Diels Alder Reaction

scholarly journals Are There Only Fold Catastrophes in the Diels–Alder Reaction Between Ethylene and 1,3–Butadiene?

2021 ◽  
Author(s):  
Leandro Ayarde-Henriquez ◽  
Cristian Guerra ◽  
Mario Duque-Noreña ◽  
Elizabeth Rincón ◽  
Patricia Pérez ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Unexpected Finding ◽  
Pericyclic Reactions ◽  
Topological Characterization ◽  
State Variable ◽  
Diels Alder Reaction ◽  
Fold Type ◽  
The One

This work revisits the topological characterization of the Diels–Alder reaction between 1,3–butadiene and ethylene. In contrast to the currently accepted rationalization, we here provide strong evidence in support of a representation in terms of seven structural stability domains separated by a sequence of 10 elementary catastrophes, but all only of the fold type, i.e., C<sub>4</sub>H<sub>6</sub> + C<sub>2</sub>H<sub>4 </sub>: 1–7– [FF]F[F<sup>†</sup>F<sup>†</sup>][F<sup>†</sup>F<sup>†</sup>][FF]F<sup>†</sup>–0 : C<sub>6</sub>H<sub>10</sub>. Such an unexpected finding provides fundamental new insights opening simplifying perspectives concerning the rationalization of the CC bond formation in pericyclic reactions in terms of the simplest Thom’s elementary catastrophe, namely the one–(state) variable, one–(control) parameter function.

Crystal structure of LepI, a multifunctional SAM-dependent enzyme which catalyzes pericyclic reactions in leporin biosynthesis

2019 ◽  
Vol 17 (8) ◽  
pp. 2070-2076 ◽  
Author(s):  
Zhenying Chang ◽  
Tamar Ansbacher ◽  
Lilan Zhang ◽  
Yong Yang ◽  
Tzu-Ping Ko ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Pericyclic Reactions ◽  
Diels Alder Reaction

Crystal structure of LepI, a SAM-dependent enzyme which can catalyze seteroselective dehydration, Diels–Alder reaction, and retro-Claisen rearrangement.

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>

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