Theoretical Exploration of Multi-Diels-Alder reaction on neutral & Li+-encapsulated C60 fullerenes

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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Natural Products Biosynthesis Involving a Putative Diels-Alder Reaction

Current Organic Chemistry ◽

10.2174/1385272820666160331234709 ◽

2016 ◽

Vol 20 (22) ◽

pp. 2421-2442 ◽

Cited By ~ 2

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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Aza-Diels-Alder Reaction: An Efficient Approach for Construction of Heterocycles

Current Organic Chemistry ◽

10.2174/1385272819666140529000155 ◽

2014 ◽

Vol 18 (12) ◽

pp. 1586-1620 ◽

Cited By ~ 10

Author(s):

Manas M. Sarmah ◽

Dipak Prajapati

Keyword(s):

Alder Reaction ◽

Diels Alder ◽

Efficient Approach ◽

Diels Alder Reaction

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Aza-Diels-Alder Reaction Between 1,2-Diaza-1,3-dienes and β-Aryl-α,β-unsaturated Carbonyl Compounds. Easy One-pot Entry to 2’-Oxo-imidazo[1’,5’- f]tetrahydropyridazine

Current Organic Synthesis ◽

10.2174/157017941006140206104854 ◽

2014 ◽

Vol 10 (6) ◽

pp. 951-960

Author(s):

Orazio Attanasi ◽

Luca Bianchi ◽

Maurizio D’Auria ◽

Gianfranco Favi ◽

Fabio Mantellini ◽

...

Keyword(s):

Carbonyl Compounds ◽

Alder Reaction ◽

Diels Alder ◽

One Pot ◽

Diels Alder Reaction

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Enantioselective Syntheses of Flavonoid Diels-Alder Natural Products: A Review

Current Organic Synthesis ◽

10.2174/1570179414666170821120234 ◽

2018 ◽

Vol 15 (2) ◽

pp. 221-229 ◽

Cited By ~ 3

Author(s):

Shah Bakhtiar Nasir ◽

Noorsaadah Abd Rahman ◽

Chin Fei Chee

Keyword(s):

Natural Products ◽

Organic Synthesis ◽

Lewis Acid ◽

Alder Reaction ◽

Diels Alder ◽

Enantioselective Synthesis ◽

Chiral Ligand ◽

Asymmetric Syntheses ◽

Diels Alder Reaction ◽

Enantioselective Syntheses

Background: The Diels-Alder reaction has been widely utilised in the syntheses of biologically important natural products over the years and continues to greatly impact modern synthetic methodology. Recent discovery of chiral organocatalysts, auxiliaries and ligands in organic synthesis has paved the way for their application in Diels-Alder chemistry with the goal to improve efficiency as well as stereochemistry. Objective: The review focuses on asymmetric syntheses of flavonoid Diels-Alder natural products that utilize chiral ligand-Lewis acid complexes through various illustrative examples. Conclusion: It is clear from the review that a significant amount of research has been done investigating various types of catalysts and chiral ligand-Lewis acid complexes for the enantioselective synthesis of flavonoid Diels-Alder natural products. The results have demonstrated improved yield and enantioselectivity. Much emphasis has been placed on the synthesis but important mechanistic work aimed at understanding the enantioselectivity has also been discussed.

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DMF. I2 Complex as Efficient Green Catalyst in the Diels-alder Reaction of Anthracene-9-Methanol with Maleimide

Current Green Chemistry ◽

10.2174/2213346104666170704112332 ◽

2017 ◽

Vol 4 (1) ◽

Cited By ~ 1

Author(s):

Urbain C. Kassehin ◽

Sèdami M. Fagla ◽

Fernand A. Gbaguidi ◽

Julien R. C. Prevost ◽

Raphaël Frédérick ◽

...

Keyword(s):

Alder Reaction ◽

Diels Alder ◽

Green Catalyst ◽

Diels Alder Reaction

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The Diels-Alder reaction of butadiene with hexacyclic olefins in the synthesis of triamantane

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19861083 ◽

1986 ◽

Vol 51 (5) ◽

pp. 1083-1085 ◽

Cited By ~ 1

Author(s):

Zdeněk Kafka ◽

Luděk Vodička

Keyword(s):

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction ◽

Important Intermediate ◽

Composition Of Products

The paper describes the composition of products arising from the Diels-Alder reaction of butadiene with hexacyclic olefins (hexacyclo[8,4,0,02,7,03,14,04,8,09,13]tetradec-5-ene and hexacyclo[6,6,0,02,6,05,14,07,12,09,13]tetradec-3-ene) under different conditions. The reaction afforded a mixture of heptacyclic olefins (heptacyclo[8,8,0,02,17,03,11,04,9,012,16,013,18]octadec-6-ene and heptacyclo[8,8,0,02,13,03,11,04,9,012,17,014,18]octadec-6-ene), which is an important intermediate in the synthesis of triamantane.

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Octafluoro[2.2]paracyclophane (AF4) Quinone

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20081764 ◽

2008 ◽

Vol 73 (12) ◽

pp. 1764-1776

Author(s):

Wei Xu ◽

William R. Dolbier ◽

Jian-Xin Duan ◽

Yian Zhai ◽

Katsu Ogawa ◽

...

Keyword(s):

Cyclic Voltammetry ◽

Reduction Potential ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction

Octafluoro[2.2]paracyclophane (AF4) has been oxidized by treatment with HIO3 in CF3CO2H to form the corresponding p-quinone along with a unique triketone. This quinone undergoes reduction to the respective hydroquinone as well as a Diels-Alder reaction with 1,3-cyclohexadiene. Its reduction potential was obtained by cyclic voltammetry and is discussed in the context of other quinones.

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