Trapping Intermediates in an [8 + 2] Cycloaddition Reaction with the Help of DFT Calculations

2011 ◽  
Vol 13 (11) ◽  
pp. 2892-2895 ◽  
Author(s):  
Marta L. Lage ◽  
Israel Fernández ◽  
Miguel A. Sierra ◽  
M. Rosario Torres
Keyword(s):  
Dft Calculations ◽  
Cycloaddition Reaction

scholarly journals When cobalt-mediated [2 + 2 + 2] cycloaddition reaction dares go astray: synthesis of unprecedented cobalt(iii)-complexes

2019 ◽  
Vol 48 (42) ◽  
pp. 15767-15771
Author(s):  
Marion Delorme ◽  
Alexander Punter ◽  
Raquel Oliveira ◽  
Corinne Aubert ◽  
Yannick Carissan ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Cycloaddition Reaction

The cobalt-mediated cycloaddition with γ-alkylidenebutenolide diverges dramatically from what is expected, leading to unprecedented polycyclic scaffold cobalt(iii)-complexes. The mechanism of this reaction has been studied by DFT calculations.

Reactivity of the superhalogen/superalkali ion encapsulated C60 fullerenes

2021 ◽  
Author(s):  
Gibu George ◽  
Anton J Stasyuk ◽  
Miquel Solà
Keyword(s):  
Dft Calculations ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Halogen Species ◽  
C60 Fullerenes

The Diels-Alder cycloaddition reaction between 1,3-cyclohexadiene and a series of C60 fullerenes with encapsulated (super)alkali/(super)halogen species (Li+@C60, Li2F+@C60, Cl-@C60, and LiF2-@C60) was explored by means of DFT calculations. Reactivity of...

scholarly journals 1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes

2020 ◽  
Author(s):  
Clotilde Philippe ◽  
Anh Thy Bui ◽  
Sabrinah Batsongo-Boulingui ◽  
ziemowit Pokladek ◽  
Katarzyna Matczyszyn ◽  
...  
Keyword(s):  
Solid State ◽  
Dft Calculations ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Reaction Sequence ◽  
Near Ir

<p>Two small 1,1,4,4-tetracyanobutadiene-functionalized chromophores were obtained by careful leverage of the regioselectivity of the cycloaddition reaction of tetracyanoethylene with anthracene-ynamide derivatives, inducing either a [2+2] or a [4+2] Diels–Alder process. DFT calculations unraveled the mechanism of the [2+2] cycloaddition-retroelectrocyclization reaction sequence with ynamides and elucidated the differing mechanisms in the two substrates. The synthesized dyes presented panchromatic absorption extending into the near-IR, and far-red/near-IR photoluminescence in the solid-state up to 1550 nm.</p>

A strategic approach to the synthesis of functionalized spirooxindole pyrrolidine derivatives: in vitro antibacterial, antifungal, antimalarial and antitubercular studies

2015 ◽  
Vol 39 (1) ◽  
pp. 520-528 ◽  
Author(s):  
Saoussen Haddad ◽  
Sarra Boudriga ◽  
Tarunkumar Nanjibhai Akhaja ◽  
Jignesh Priyakant Raval ◽  
François Porzio ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Biological Activities ◽  
Cycloaddition Reaction ◽  
Strategic Approach

A series of spirooxindole pyrrolidine derivatives has been synthesized and evaluated for theirin vitrobiological activities. The observed regio- and stereoselectivity of the cycloaddition reaction has been rationalized using DFT calculations.

scholarly journals On the Question of Zwitterionic Intermediates in the [3 + 2] Cycloaddition Reactions between C-arylnitrones and Perfluoro 2-Methylpent-2-ene

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7147
Author(s):  
Katarzyna Mitka ◽  
Katarzyna Fela ◽  
Aleksandra Olszewska ◽  
Radomir Jasiński
Keyword(s):  
Dft Calculations ◽  
Molecular Mechanism ◽  
Intermolecular Interactions ◽  
Cycloaddition Reaction ◽  
Reaction Centers ◽  
Cycloaddition Reactions ◽  
Reaction Paths ◽  
One Step ◽  
Step Mechanism

The molecular mechanism of the [3 + 2] cycloaddition reaction between C-arylnitrones and perfluoro 2-methylpent-2-ene was explored on the basis of DFT calculations. It was found that despite the polar nature of the intermolecular interactions, as well as the presence of fluorine atoms near the reaction centers, all reactions considered cycloaddition proceed via a one-step mechanism. All attempts for the localization of zwitterionic intermediates on the reaction paths were not successful. Similar results were obtained regardless of the level of theory applied.

Unexpected radical mechanism in a [4+1] cycloaddition reaction

2021 ◽  
Author(s):  
István Bors ◽  
Mihály Purgel ◽  
Péter Pál Fehér ◽  
Tamás Varga ◽  
Gábor Speier ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Cycloaddition Reaction ◽  
Radical Mechanism ◽  
Radical Intermediates

The mechanism of the cheletropic reaction of monoimines with PPh3via unexpected radical intermediates resulting in oxazaphospholes has been discussed based on EPR, UV-vis and DFT calculations.

scholarly journals Regio- and Stereoselectivity in the 1,3-Dipolar Cycloaddition Reactions of Isoquinolinium Ylides with Cyclopenta[a]acenaphthylen-8-ones

Synlett ◽  
2020 ◽  
Vol 31 (17) ◽  
pp. 1691-1695
Author(s):  
Issa Yavari ◽  
Parisa Ravaghi ◽  
Maryam Safaei ◽  
Jasmine Kayanian
Keyword(s):  
Dft Calculations ◽  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Diastereoselective Synthesis ◽  
X Ray

AbstractA convenient regio- and diastereoselective synthesis of functionalized 5a,5b-dihydro-5H,13H-naphtho[1′′,8′′:4′,5′,6′]pentaleno[1′:3,4]pyrrolo[2,1-a]isoquinolin-5-ones via 1,3-dipolar cycloaddition reaction of 8H-cyclopenta[a]acenaphthylen-8-ones with carbonyl-stabilized isoquinolinium N-ylides, is described. Based on DFT calculations at b3lyp/6-311+g(d,p) level of theory, a nonconcerted mechanism is proposed to explain the regioselectivity of this reaction. The structure of a typical product was confirmed by X-ray crystallographic analysis.

Synthesis of novel dispiropyrrolothiazoles by three-component 1,3-dipolar cycloaddition and evaluation of their antimycobacterial activity

RSC Advances ◽  
2014 ◽  
Vol 4 (103) ◽  
pp. 59462-59471 ◽  
Author(s):  
Saoussen Haddad ◽  
Sarra Boudriga ◽  
François Porzio ◽  
Armand Soldera ◽  
Moheddine Askri ◽  
...  
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Dft Calculations ◽  
Cycloaddition Reaction ◽  
Antimycobacterial Activity ◽  
Dipolar Cycloaddition

A series of dispiropyrrolothiazoles derivatives has been synthesized screenedin vitroagainstMycobacterium tuberculosisH37Rv. The observed regio- and stereoselectivity of the cycloaddition reaction has been rationalized by DFT calculations.

scholarly journals 1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes

2020 ◽  
Author(s):  
Clotilde Philippe ◽  
Anh Thy Bui ◽  
Sabrinah Batsongo-Boulingui ◽  
ziemowit Pokladek ◽  
Katarzyna Matczyszyn ◽  
...  
Keyword(s):  
Solid State ◽  
Dft Calculations ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Reaction Sequence ◽  
Near Ir

<p>Two small 1,1,4,4-tetracyanobutadiene-functionalized chromophores were obtained by careful leverage of the regioselectivity of the cycloaddition reaction of tetracyanoethylene with anthracene-ynamide derivatives, inducing either a [2+2] or a [4+2] Diels–Alder process. DFT calculations unraveled the mechanism of the [2+2] cycloaddition-retroelectrocyclization reaction sequence with ynamides and elucidated the differing mechanisms in the two substrates. The synthesized dyes presented panchromatic absorption extending into the near-IR, and far-red/near-IR photoluminescence in the solid-state up to 1550 nm.</p>

Sign in / Sign up

Export Citation Format

Share Document