Modern Valence-Bond Description of Chemical Reaction Mechanisms:  Diels−Alder Reaction

1998 ◽  
Vol 120 (16) ◽  
pp. 3975-3981 ◽  
Author(s):  
Peter B. Karadakov ◽  
David L. Cooper ◽  
Joseph Gerratt
Keyword(s):  
Chemical Reaction ◽  
Reaction Mechanisms ◽  
Valence Bond ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Chemical Reaction Mechanisms

Diels‐Alder reaction mechanisms of substituted chiral anthracene: A theoretical study based on the reaction force and reaction electronic flux

2020 ◽  
Vol 41 (23) ◽  
pp. 2022-2032 ◽  
Author(s):  
Jennifer Paola Hernández Mancera ◽  
Francisco Núñez‐Zarur ◽  
Soledad Gutiérrez‐Oliva ◽  
Alejandro Toro‐Labbé ◽  
Ricardo Vivas‐Reyes
Keyword(s):  
Reaction Mechanisms ◽  
Theoretical Study ◽  
Reaction Force ◽  
Alder Reaction ◽  
Diels Alder ◽  
Reaction Electronic Flux ◽  
Diels Alder Reaction

scholarly journals Ion mobility spectrometry-tandem mass spectrometry strategies for the on-line monitoring of a continuous microflow reaction

2021 ◽  
Author(s):  
Darya Hadavi ◽  
Peiliang Han ◽  
Maarten Honing
Keyword(s):  
Mass Spectrometry ◽  
Tandem Mass Spectrometry ◽  
Chemical Reaction ◽  
Ion Mobility ◽  
Alder Reaction ◽  
Diels Alder ◽  
Tandem Mass ◽  
Diels Alder Reaction ◽  
On Line ◽  
Line Analysis

AbstractContinuous flow chemistry is an efficient, sustainable and green approach for chemical synthesis that surpasses some of the limitations of the traditional batch chemistry. Along with the multiple advantages of a flow reactor, it could be directly connected to the analytical techniques for on-line monitoring of a chemical reaction and ensure the quality by design. Here, we aim to use ion mobility, mass and tandem mass spectrometry (IMS-MS and MS/MS) for the on-line analysis of a pharmaceutically relevant chemical reaction. We carried out a model hetero-Diels Alder reaction in a microflow reactor directly connected to the IMS-MS and MS/MS using either electrospray or atmospheric pressure photo ionization methods. We were able to monitor the reaction mechanism of the Diels Alder reaction and structurally characterize the reaction product and synthesis side-products. The chosen approach enabled identification of two isomers of the main reaction product. A new strategy to annotate the ion mobility spectrum in the absence of standard molecules was introduced and tested for its validity. This was achieved by determining the survival yield of each isomer upon ion mobility separation and density functional theory calculations. This approach was verified by comparing the theoretically driven collision cross section values to the experimental data. In this paper, we demonstrated the potential of combined IMS-MS and MS/MS on-line analysis platform to investigate, monitor and characterize structural isomers in the millisecond time scale.

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>

Sign in / Sign up

Export Citation Format

Share Document