Struktur und Reaktivität von isoanellierten heterocyclischen Systemen mit 4nπ- und (4n+2)π-Elektronen, XVII [1] Diels-Aider- und Michael-Additionsreaktionen von 3-Alkoxy-2,4-dihydropyrrolo[3,4-b]indolen mit Ethindicarbonsäuredialkylestern / Structure and Reactivity of Isoannelated Heterocyclic Systems with 4nπ- and (4n+2)π-Electrons, XVII [1] Diels-Alder and Michael Addition Reactions of 3-Alkoxy-2,4-dihydropyrrolo[3,4-b]indoles with Dialkyl Acetylenedicarboxylates

1988 ◽  
Vol 43 (12) ◽  
pp. 1656-1661 ◽  
Author(s):  
Gerald Dyker ◽  
Richard P. Kreher
Keyword(s):  
Michael Addition ◽  
Isotopic Labeling ◽  
Alder Reaction ◽  
Diels Alder ◽  
Addition Reactions ◽  
Current Interest ◽  
Polar Solvents ◽  
Dialkyl Acetylenedicarboxylates ◽  
Diels Alder Reaction

Abstract The reactions of 2-rm-butyl-3-methoxy-4-methyl-2,4-dihydropyrrolo[3,4-b]indole (3) with dialkyl acetylenedicarboxylates are decisively influenced by the solvent. In the presence of alcohols as protic and polar solvents Michael addition is prefered, while in aprotic and less polar solvents like ether the Diels-Alder reaction is favoured. Based on stereospecific hydrolysis and isotopic labeling dipolar intermediates are discussed. The results are of current interest for mechanistic and theoretical reasons

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.

Self-crosslinkable polymers from furan-functionalized Meldrum's acid and maleimides as effective precursors of free-standing and flexible crosslinked polymer films showing low dielectric constants

2020 ◽  
Vol 11 (9) ◽  
pp. 1606-1613 ◽  
Author(s):  
Chien-Ho Huang ◽  
Ying-Ling Liu
Keyword(s):  
Polymer Films ◽  
Michael Addition ◽  
Alder Reaction ◽  
Diels Alder ◽  
Dielectric Constants ◽  
Free Standing ◽  
Crosslinked Polymer ◽  
Low Dielectric ◽  
Diels Alder Reaction ◽  
Reactive Polymers

The integration of Michael addition and Diels–Alder reaction in the synthesis of reactive polymers for self-standing and flexible crosslinked polymer films.

Design and synthesis of tetraazachlorins, tetraazabacteriochlorins and tetraazaisobacteriochlorins

2009 ◽  
Vol 13 (02) ◽  
pp. 188-202 ◽  
Author(s):  
Elena A. Makarova ◽  
Evgeny A. Lukyanets
Keyword(s):  
Dicarboxylic Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Azomethine Ylides ◽  
Addition Reactions ◽  
Dipolar Cycloadditions ◽  
Design And Synthesis ◽  
Diels Alder Reaction ◽  
Oxidation Resistant ◽  
Derivatives Of

Three approaches to the synthesis of reduced derivatives of tetraazaporphine such as tetraazachlorin, tetraazabacteriochlorin, and tetraazaisobacteriochlorin are reviewed. The first synthesis of alkyl-substituted tetraazachlorins was achieved by the catalytic hydrogenation of magnesium complexes of tetraazaporphines. Two other synthesis approaches for reduced tetraazaporphines based on the mixed condensation of the precursors with different hydrogenation levels and β–β addition reactions have been developed in the last decade. The use of tetramethylsuccinonitrile as the saturated component in the mixed condensation with derivatives of aromatic and heteroaromatic dicarboxylic acids enable the synthesis of oxidation-resistant benzo-; 1,2- and 2,3-naphtho-; pyrazino-; 2,3- and 3,4-pyridino-fused tetraazachlorins, tetraazabacteriochlorins, and tetraazaisobacteriochlorins. Fullerene conjugates of reduced tetraazaporphine derivatives were obtained using 1,2-dicyanofullerene as the source of the hydrogenated sites. Tetraazaporphine can act as dienophile in Diels-Alder reaction with dienes of the anthracene and cyclopentadiene series and also as dipolarophile in 1,3-dipolar cycloadditions with azomethine ylides and nitrones. In addition, the effect of the reduction of peripheral double bonds in tetraazaporphine macrocycle alone, and in combination with annelation of benzene or heterocyclic rings on the absorption spectra is discussed.

Synthesis of functionalized benzene using Diels–Alder reaction of activated acetylenes with synthesized phosphoryl-2-oxo-2H-pyran

2015 ◽  
Vol 70 (5) ◽  
pp. 355-360 ◽  
Author(s):  
Zinatossadat Hossaini ◽  
Faramarz Rostami-Charati ◽  
Fatemeh Sheikholeslami-Farahani ◽  
Mahboubeh Ghasemian
Keyword(s):  
Good Yield ◽  
Alder Reaction ◽  
Diels Alder ◽  
Benzene Derivatives ◽  
One Pot ◽  
Dialkyl Acetylenedicarboxylates ◽  
Diels Alder Reaction ◽  
Alkyl Bromides ◽  
Solvent Free Conditions ◽  
Trialkyl Phosphites

AbstractAn effective one-pot synthesis of benzene derivatives using a Diels–Alder reaction of activated acetylenes with phosphoryl-2-oxo-2H-pyrans is described. The latter compounds were synthesized in good yield via the reaction of dialkyl acetylenedicarboxylates and alkyl bromides in the presence of trialkyl phosphites under solvent-free conditions at 50 oC.

Microwave Thermal Effect on Diels-Alder Reaction of Furan and Maleimide

2020 ◽  
Vol 7 (1) ◽  
pp. 67-73 ◽  
Author(s):  
Simin Sun ◽  
Chong Teng ◽  
Jiaxi Xu
Keyword(s):  
Thermal Effect ◽  
Hot Spots ◽  
Arrhenius Equation ◽  
Activation Energies ◽  
Alder Reaction ◽  
Diels Alder ◽  
Molecular Probe ◽  
Polar Solvents ◽  
Diels Alder Reaction ◽  
Higher Temperature

Background: Higher temperature regions (hot spots) have been observed in organic reactions and are attributed to microwave selective heating. The accumulated heat in reaction systems accelerates certain reactions. Methods: The theoretical calculation was applied to select a suitable Diels-Alder reaction as a molecular probe to determine the microwave thermal effect on Diels-Alder reaction, one class of bimolecular reactions. The kinetic investigations were utilized to determine the reaction activation energies and further to calculate the actual reaction temperatures under different microwave conditions from the Arrhenius equation. Results: On the basis of the theoretical calculational results, Diels-Alder reaction of furan and maleimide was selected as a molecular probe to determine the microwave thermal effect in Diels- Alder reaction. Their activation energies under thermal conditions were determined from kinetic data by using the Arrhenius equation. The actual reaction temperatures under different microwave conditions were further deduced from their activation energies and the Arrhenius equation. Conclusion: Higher temperature regions (hot spots) were observed in Diels-Alder reaction, and they are more obvious in less polar solvents than those in more polar solvents in the microwave irradiated reactions.

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