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.

Synthesis and properties of a novel Cu(ii)–pyridineoxazoline containing polymeric catalyst for asymmetric Diels–Alder reaction

RSC Advances ◽  
2015 ◽  
Vol 5 (4) ◽  
pp. 2882-2890 ◽  
Author(s):  
Heng Wang ◽  
Na Li ◽  
Zijia Yan ◽  
Jie Zhang ◽  
Xinhua Wan
Keyword(s):  
Molecular Mass ◽  
Reaction Rate ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Polymeric Catalyst

Soluble and recyclable Cu(ii)–pyridineoxazoline containing polymeric catalyst shows faster reaction rate and higher enantio-selectivity than its low molecular mass counterpart in D–A reaction of 2-alkenoyl pyridine N-oxide and cyclopentadiene.

scholarly journals The effect of Lewis acids on the intramolecular Diels–Alder reaction of the furan diene

1992 ◽  
Vol 70 (12) ◽  
pp. 2929-2947 ◽  
Author(s):  
Christine Rogers ◽  
Brian A. Keay
Keyword(s):  
Carbon Atom ◽  
Lewis Acid ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Oxygen Bridge ◽  
Excellent Yield ◽  
Diels Alder Reaction ◽  
Alkyl Groups ◽  
General Method

A general method is described for effecting the intramolecular Diels–Alder reaction of the furan diene in which the side arm connecting the diene to the dienophile contains four carbon atoms. The use of 1.1 equivalents of methylaluminum dichloride at −78 °C for 2–8 h shifts the Diels–Alder equilibrium towards the products and provides the oxatricyclo adducts in good to excellent yield. Catalytic quantities of methylaluminum dichloride (10 mol%) provided a higher quantity of adduct than excess Lewis acid when the enone was substituted with alkyl groups. The scope was extended to include a precursor containing a five carbon atom side arm, and two examples containing acetylenic dienophiles that were activated by a carbonyl moiety on the side arm. Precursors having a four carbon atom side arm provided only oxatricyclo adducts having the side arm syn to the oxygen bridge. The assignment of the stereochemistry of the oxatricyclo adducts is discussed in detail.

Stereocontrolled construction of A.B.C.[6.6.6] tricycle via transannular Diels–Alder reaction of 14-membered triene macrocycle

1990 ◽  
Vol 68 (12) ◽  
pp. 2144-2152 ◽  
Author(s):  
Michel Cantin ◽  
Yao-Chang Xu ◽  
Pierre Deslongchamps
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Excellent Yield ◽  
Diels Alder Reaction ◽  
Tricyclic Compound ◽  
Stereocontrolled Synthesis

The synthesis of the four acyclic trienes 11a, b and 20a, b is reported. The tandem macrocyclization and stereoselective transannular Diels–Alder reaction of acyclic trienes 11b (trans-trans-cis) and 20b (trans-trans-trans) were observed in the presence of Cs2CO3 at 85 °C to give tricycles 30 (TST) and 32 (CAT) respectively. However, treatment of acyclic trienes 11a (cis-trans-cis) and 20a (cis-trans-trans) under the same conditions yielded the 14-membered macrocycles 21 and 23, which were stereoselectively transformed at 250 °C into tricycles 22 (CST) and 24 (CAT) respectively in excellent yield. Keywords: stereocontrolled synthesis, macrocycle, tricyclic compound, transannular Diels–Alder reaction.

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...

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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