Unexpected Diels-Alder reaction of [60]fullerene with electron-deficient ferrocenes as cyclopentadiene surrogates

2021 ◽  
Author(s):  
Guan-Wu Wang ◽  
Zhan Liu ◽  
Zheng-Chun Yin ◽  
Wen-Qiang Lu ◽  
Dian-Bing Zhou
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Fullerene C60 ◽  
Mechanistic Studies ◽  
Diels Alder Reaction

The unexpected Diels–Alder reaction of [60]fullerene (C60) with ferrocenes bearing electron-withdrawing groups as cyclopentadiene surrogates has been developed to selectively afford single isomers of [2+4] cycloadducts of C60. Mechanistic studies...

scholarly journals Diels–Alder cycloaddition and RAFT chain end functionality: an elegant route to fullerene end-capped polymers with control over molecular mass and architecture

2017 ◽  
Vol 8 (18) ◽  
pp. 2796-2805 ◽  
Author(s):  
Anna Isakova ◽  
Christian Burton ◽  
Daniel J. Nowakowski ◽  
Paul D. Topham
Keyword(s):  
Molecular Mass ◽  
Alder Reaction ◽  
Diels Alder ◽  
Fullerene C60 ◽  
Composition Control ◽  
Excellent Yield ◽  
Diels Alder Reaction

Fullerene C60 end-capped polymers are synthesised using RAFT chain end functionality and Diels–Alder reaction with excellent yield and composition control.

Mechanistic studies of a CAB-catalyzed asymmetric Diels-Alder reaction

1993 ◽  
Vol 115 (22) ◽  
pp. 10412-10413 ◽  
Author(s):  
Kazuaki Ishihara ◽  
Qingzhi Gao ◽  
Hisashi Yamamoto
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Mechanistic Studies ◽  
Diels Alder Reaction

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>

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