Rationalisation of Solvent Effects in the DielsAlder Reaction Between Cyclopentadiene and Methyl Acrylate in Room Temperature Ionic Liquids

2005 ◽  
Vol 347 (2-3) ◽  
pp. 266-274 ◽  
Author(s):  
Ana Vidiš ◽  
C. André Ohlin ◽  
Gábor Laurenczy ◽  
Ernst Küsters ◽  
Gottfried Sedelmeier ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Solvent Effects ◽  
Methyl Acrylate ◽  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Room Temperature Ionic Liquids ◽  
Diels Alder Reaction

High-pressure effects on the Diels–Alder reaction in room temperature ionic liquids

2007 ◽  
Vol 20 (2) ◽  
pp. 109-114 ◽  
Author(s):  
Ana Vidiš ◽  
Gábor Laurenczy ◽  
Ernst Küsters ◽  
Gottfried Sedelmeier ◽  
Paul J. Dyson
Keyword(s):  
High Pressure ◽  
Ionic Liquids ◽  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Pressure Effects ◽  
Room Temperature Ionic Liquids ◽  
Diels Alder Reaction ◽  
High Pressure Effects

scholarly journals Ionic liquid promoted Diels-Alder Reaction between anthrone and maleimides

2010 ◽  
Vol 8 (2) ◽  
pp. 356-360 ◽  
Author(s):  
Nitin Mirgane ◽  
Sandip Kotwal ◽  
Anil Karnik
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Room Temperature ◽  
Alder Reaction ◽  
Dual Role ◽  
Diels Alder ◽  
Environmentally Benign ◽  
Green Solvents ◽  
Imidazolium Ionic Liquid ◽  
Diels Alder Reaction

AbstractIonic liquids (IL) are gaining importance as green solvents. Imidazolium ionic liquid [bmim]+[Cl]−, an environmentally benign solvent, was found to promote the Diels-Alder reaction between anthrone and maleimides at room temperature with excellent yields. The ionic liquid played a dual role as solvent and catalyst.

scholarly journals Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

2015 ◽  
Vol 11 ◽  
pp. 576-582 ◽  
Author(s):  
Grzegorz Mlostoń ◽  
Paulina Grzelak ◽  
Maciej Mikina ◽  
Anthony Linden ◽  
Heinz Heimgartner
Keyword(s):  
High Pressure ◽  
Room Temperature ◽  
Thermal Conditions ◽  
Alder Reaction ◽  
Diels Alder ◽  
Hydrogen Shift ◽  
Diels Alder Reaction ◽  
Shift Sequence

Selected hetaryl and aryl thioketones react with acetylenecarboxylates under thermal conditions in the presence of LiClO4 or, alternatively, under high-pressure conditions (5 kbar) at room temperature yielding thiopyran derivatives. The hetero-Diels–Alder reaction occurs in a chemo- and regioselective manner. The initially formed [4 + 2] cycloadducts rearrange via a 1,3-hydrogen shift sequence to give the final products. The latter were smoothly oxidized by treatment with mCPBA to the corresponding sulfones.

Influence of Lewis Acids on the Diels–Alder Reaction. IV. Reaction of 2-Methyl- and 2-Phenylfuran with Ethyl Propiolate

1971 ◽  
Vol 49 (19) ◽  
pp. 3152-3157 ◽  
Author(s):  
A. W. Mcculloch ◽  
A. G. McInnes
Keyword(s):  
Methyl Acrylate ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Methyl Propionate ◽  
Diels Alder Reaction ◽  
By Products

The AlCl3-promoted reactions of 2-methyl- and of 2-phenylfuran with ethyl propiolate afford as major products ethyl 5-hydroxy-2-methyl- and 2-phenylbenzoates (6a, 6b). Also isolated as minor by-products of these reactions are ethyl 3-(2-furyl-5-methyl)acrylate (5a), ethyl 3-(2-furyl-5-phenyl)acrylate (5b), ethyl 3,3-di(2-furyl-5-methyl)propionate (10a), ethyl 3,3-di(2-furyl-5-phenyl)propionate (10b), and ethyl 2-hydroxy-5-methylbenzoate (8a).

scholarly journals Enhancing the reactivity of 1,2-diphospholes in cycloaddition reactions

2015 ◽  
Vol 11 ◽  
pp. 169-173 ◽  
Author(s):  
Almaz Zagidullin ◽  
Vasili Miluykov ◽  
Elena Oshchepkova ◽  
Artem Tufatullin ◽  
Olga Kataeva ◽  
...  
Keyword(s):  
Room Temperature ◽  
Cycloaddition Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Alkyl Halides ◽  
Ethyl Iodide ◽  
Para Position ◽  
Cycloaddition Reactions ◽  
Diels Alder Reaction ◽  
Heating Up

Two different approaches have been employed to enhance the reactivity of 1-alkyl-1,2-diphospholes – the introduction of electron-withdrawing groups either at the phosphorus atoms or in the para-position of the arene ring. The alkylation of sodium 1,2-diphospha-3,4,5-triphenylcyclopentadienide with alkyl halides Hal-CH2-R (R = CN, COOEt, OMe, CH2OEt) results in corresponding 1-alkyl-3,4,5-triphenyl-1,2-diphospholes (alkyl = CH2CN (1a), CH2COOEt (1b), CH2OMe (1c), and (CH2)2OEt (1d)), which spontaneously undergo the intermolecular [4 + 2] cycloaddition reactions at room temperature to form the mixture of the cycloadducts, 2a–c, respectively. However the alkylation of sodium 1,2-diphospha-3,4,5-tri(p-fluorophenyl)cyclopentadienide with ethyl iodide leads to stable 1-ethyl-3,4,5-tris(p-fluorophenyl)-1,2-diphosphole (1e), which forms the [4 + 2] cycloadduct 2,3,4,4a,5,6-hexa(p-fluorophenyl)-1-ethyl-1,7,7a-triphospha-4,7-(ethylphosphinidene)indene (2e) only upon heating up to 60 °C. With further heating to 120 °C with N-phenylmaleimide, the cycloadducts 2a–c and 2e undergo the retro-Diels–Alder reaction and form only one product of the [4 + 2] cycloaddition reaction 3a–с, 3e with good yields up to 65%.

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