Nazarov Cyclization and Oxo-Diels–Alder Reaction of Chalcones Induced by the Naked Silver Cation in Gas Phase

2013 ◽  
Vol 32 (11) ◽  
pp. 3385-3390 ◽  
Author(s):  
Hezhi Sun ◽  
Yunfeng Chai ◽  
Lin Wang ◽  
Kezhi Jiang ◽  
Yuanjiang Pan
Keyword(s):  
Gas Phase ◽  
Alder Reaction ◽  
Diels Alder ◽  
Silver Cation ◽  
Nazarov Cyclization ◽  
Diels Alder Reaction

Gas-Phase negative ion hetero retro-diels-alder reaction

1991 ◽  
Vol 26 (7) ◽  
pp. 669-670 ◽  
Author(s):  
David J. Burinsky ◽  
Richard Dunphy ◽  
J. Douglas Alvessantana ◽  
Mary Lou Cotter
Keyword(s):  
Gas Phase ◽  
Alder Reaction ◽  
Diels Alder ◽  
Negative Ion ◽  
Diels Alder Reaction

Gas-phase Diels-Alder reaction of the o-quinodimethane radical cation and neutral styrene

1983 ◽  
Vol 48 (9) ◽  
pp. 1522-1527 ◽  
Author(s):  
Edward K. Chess ◽  
Ping Huang Lin ◽  
Michael L. Gross
Keyword(s):  
Gas Phase ◽  
Radical Cation ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

DFT studies on the diastereoselectivity and regioselectivity of multicomponent domino Knoevenagel/Diels–Alder reaction

2020 ◽  
Vol 19 (02) ◽  
pp. 2050005 ◽  
Author(s):  
Mina Attarbashi ◽  
Nader Zabarjad Shiraz ◽  
Marjaneh Samadizadeh
Keyword(s):  
Gas Phase ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ring Closure ◽  
Dft Studies ◽  
Acid Base ◽  
Bond Rotation ◽  
Diels Alder Reaction ◽  
Difference Formula ◽  
State Formula

In this study, mechanism and stereochemistry of multicomponent domino Knoevenagel/Diels–Alder reaction were investigated theoretically. Structures of reagents, transition states, intermediates, and products were optimized at M062X/6-31[Formula: see text]G(d,p) level of theory. Although the mechanism of this reaction involved several processes, including bond rotation, isomerization, asymmetric cycloaddition, acid-base, and nucleophile–electrophile competitions, critical processes were studied to provide a clearer picture of the mechanism of this valuable reaction in terms of stereochemistry considerations. According to the results, the ring closure step of reaction performed via a polar Dield-Alder mechanism, having enthalpy at approximately 40[Formula: see text]kcal/mol. The diastereoselectivity of the reaction was controlled by the interaction of dienophile with the less hindered face of diene through a more stable endo transition state ([Formula: see text] and 27.31 in methanol and gas phase, respectively). HSAB criteria could explain the regioselectivity of this reaction by considering the least softness difference ([Formula: see text]) for interacting C-atoms based on Hirshfeld populations. The result was the creation of cis-spiro cyclohexanone under kinetic and thermodynamic controls as a predominant diastereoselective and regioselective product.

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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