scholarly journals Origins of stereoselectivity in uncatalyzed and ZnBr2-catalyzed Diels–Alder reactions of a chiral sulfinylquinone

2019 ◽  
Vol 17 (38) ◽  
pp. 8756-8767
Author(s):  
Ka Ho Chow ◽  
Elizabeth H. Krenske
Keyword(s):  
Dft Calculations ◽  
Diels Alder ◽  
Sulfinyl Group

DFT calculations show how a chiral sulfinyl group differentiates the diastereotopic faces of an adjacent CC bond in quinone Diels–Alder reactions.

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>

Influence of the Sulfinyl Group on the Chemoselectivity and π-Facial Selectivity of Diels−Alder Reactions of(S)-2-(p-Tolylsulfinyl)-1,4-benzoquinone

1996 ◽  
Vol 61 (2) ◽  
pp. 503-509 ◽  
Author(s):  
M. Carmen Carreño ◽  
José L. García Ruano ◽  
Miguel A. Toledo ◽  
Antonio Urbano ◽  
Cynthia Z. Remor ◽  
...  
Keyword(s):  
Diels Alder ◽  
Facial Selectivity ◽  
Sulfinyl Group

DFT calculations induced a regiochemical outcome revision of the Diels–Alder reaction between levoglucosenone and isoprene

2011 ◽  
Vol 52 (24) ◽  
pp. 3116-3119 ◽  
Author(s):  
Ariel M. Sarotti ◽  
Alejandra G. Suárez ◽  
Rolando A. Spanevello
Keyword(s):  
Dft Calculations ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Remote regio- and stereocontrol by the sulfinyl group: Diels–Alder reaction of sulfinyl dienols and 8,8-dimethylnaphthalene-1,4,5(8H)-trione

2013 ◽  
Vol 24 (1) ◽  
pp. 56-61 ◽  
Author(s):  
Iriux Almodovar ◽  
Wilson Cardona ◽  
Tomás Delgado-Castro ◽  
Gerald Zapata-Torres ◽  
Marcos Caroli Rezende ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Sulfinyl Group

Reactivity descriptor for the retro Diels–Alder reaction of partially saturated 2-pyrones: DFT study on substituents and solvent effects

RSC Advances ◽  
2016 ◽  
Vol 6 (103) ◽  
pp. 101697-101706 ◽  
Author(s):  
Tuhin S. Khan ◽  
Shelaka Gupta ◽  
Md. Imteyaz Alam ◽  
M. Ali Haider
Keyword(s):  
Density Functional Theory ◽  
Dft Calculations ◽  
Density Functional ◽  
Alder Reaction ◽  
Diels Alder ◽  
Polar Solvents ◽  
Functional Theory ◽  
Partially Saturated ◽  
Diels Alder Reaction ◽  
Reactivity Descriptor

​The retro-Diels–Alder (rDA) reaction of partially saturated 2-pyrones were studied using density functional theory (DFT) calculations in polar and non-polar solvents, and fundamental descriptors were proposed to understand the electronic and solvent effect.

Influence of Non-Covalent Interactions in the Exo- and Regioselectivity of Aza-Diels–Alder Reactions: Experimental and DFT Calculations

2019 ◽  
Vol 84 (17) ◽  
pp. 10825-10831 ◽  
Author(s):  
Sebastián Gallardo-Fuentes ◽  
Nicolás Lezana ◽  
Susan Lühr ◽  
Antonio Galdámez ◽  
Marcelo Vilches-Herrera
Keyword(s):  
Dft Calculations ◽  
Diels Alder ◽  
Non Covalent Interactions ◽  
Covalent Interactions

Photo-NHC Catalysis: Accessing Ketone Photochemistry with Carboxylic Acid Derivatives

Synlett ◽  
2020 ◽  
Author(s):  
Matthew N. Hopkinson ◽  
Andreas Mavroskoufis
Keyword(s):  
Carboxylic Acid ◽  
Dft Calculations ◽  
Diels Alder ◽  
Acid Oxidation ◽  
Proof Of Concept ◽  
Carbonyl Groups ◽  
Td Dft ◽  
Aldehydes And Ketones ◽  
Novel Strategy ◽  
Acid Fluorides

AbstractExcitation of carbonyl groups is one of the most widely employed activation modes in photochemistry. Many synthetically important transformations, however, are successful only with aldehydes and ketones; substrates at the carboxylic acid oxidation level remain underrepresented. We have developed a conceptually novel strategy for enabling ‘ketone-like’ photochemistry with carboxylic acid derivatives that employs an N-heterocyclic carbene (NHC) organocatalyst. Using this ‘Photo-NHC’ catalysis approach, a proof-of-concept photoenolization/Diels–Alder (PEDA) reaction between acid fluorides and trifluoroacetophenones was developed. Stoichiometric studies and TD-DFT calculations supported a mechanistic scenario in which the NHC influences the absorption wavelength and inherent photochemical reactivity of the carbonyl group during the catalytic cycle.1 Introduction2 Photo-NHC Catalysis3 Conclusions

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