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Search for "electron-deficient ethenes" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies

Grzegorz Mlostoń and
Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 2235–2251, doi:10.3762/bjoc.13.221

reactions; electron-deficient ethenes; heterocyclization reactions; Michael additions; SET mechanism; Review Introduction Electron-deficient alkenes form an important class of organic compounds, which are of key importance in organic synthesis. The best known representative of this class is

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Graphical Abstract

Figure 1: Dialkyl dicyanofumarates E-1 and dicyanomaleates Z-1.

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Scheme 1: Methods for the synthesis of dialkyl dicyanofumarates E-1 from alkyl cyanoacetates 2.

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Scheme 2: Methods for the synthesis of dialkyl dicyanofumarates E-1 from alkyl bromoacetates 3.

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Scheme 3: Reaction of dimethyl dicyanofumarate (E-1b) with dimethoxycarbene [(MeO)₂C:] generated in situ from...

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Scheme 4: Cyclopropanation of diethyl dicyanofumarate (E-1a) through reaction with the thiophene derived sulf...

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Scheme 5: Cyclopropanation of dimethyl dicyanofumarate (E-1b) through a stepwise reaction with the in situ ge...

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Scheme 6: The [2 + 2]-cycloadditions of dimethyl dicyanofumarate (E-1b) with electron-rich ethylenes 20 and 22...

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Scheme 7: The [2 + 2]-cycloaddition of isomeric dimethyl dicyanofumarate (E-1b) and dicyanomaleate (Z-1b) wit...

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Scheme 8: Non-concerted [2 + 2]-cycloaddition between E-1b and bicyclo[2.1.0]pentene (27).

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Scheme 9: Stepwise [3 + 2]-cycloadditions of some thiocarbonyl S-methanides with dialkyl dicyanofumarates E-1...

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Scheme 10: Stepwise [3 + 2]-cycloadditions of dimethyl dicyanofumarate (E-1b) and dimethyl dicyanomaleate (Z-1b...

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Scheme 11: [3 + 2]-Cycloaddition of diazomethane with dimethyl dicyanofumarate (E-1b) leading to 1H-pyrazole d...

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Scheme 12: Reversible Diels–Alder reaction of fulvenes 36 with diethyl dicyanofumarate (E-1a).

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Scheme 13: [4 + 2]-Cycloaddition of 9,10-dimethylanthracene (39b) and E-1a.

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Scheme 14: Stepwise [4 + 2]-cycloaddition of dimethyl dicyanofumarate (E-1b) with electron-rich 1,1-dimethoxy-...

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Scheme 15: Formal [4 + 2]-cycloaddition of 3,4-di(α-styryl)furan (47) with dimethyl dicyanofumarate (E-1b).

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Scheme 16: Acid-catalyzed Michael addition of enolizable ketones of type 49 to E-1.

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Scheme 17: Reaction of diethyl dicyanofumarate (E-1a) with ammonia NH₃.

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Scheme 18: Reaction of dialkyl dicyanofumarates E-1 with primary and secondary amines.

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Scheme 19: Reaction of dialkyl dicyanofumarates E-1 with 1-azabicyclo[1.1.0]butanes 55.

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Scheme 20: Formation of pyrazole derivatives in the reaction of hydrazines with E-1.

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Scheme 21: Formation of 5-aminopyrazole-3,4-dicarboxylate 65 via heterocyclization reactions.

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Scheme 22: Reactions of aryl- and hetarylcarbohydrazides 67 with E-1a.

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Scheme 23: Multistep reaction leading to perhydroquinoxaline derivative 73.

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Scheme 24: Synthesis of ethyl 7-aminopteridin-6-carboxylates 75 via a domino reaction.

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Scheme 25: Synthesis of morhpolin-2-ones 80 from E-1 and β-aminoalcohols 78 through an initial aza-Michael add...

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Scheme 26: Reaction of 3-amino-5-arylpyrazoles 81 with dialkyl dicyanofumarates E-1 via competitive nucleophil...

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Scheme 27: Heterocyclization reaction of thiosemicarbazone 86 with E-1a.

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Scheme 28: Formation of diethyl 4-cyano-5-oxotetrahydro-4H-chromene-3,4-dicarboxylate (90) from E-1a via heter...

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Scheme 29: Reaction of dialkyl dicyanofumarates E-1 with cysteamine (92).

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Scheme 30: Formation of disulfides through reaction of thiols with E-1a.

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Scheme 31: Formation of CT salts of E-1 with Mn²⁺ and Cr²⁺ metallocenes through one-electron transfer.

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Scheme 32: Oxidation of diethyl dicyanofumarate (E-1a) with H₂O₂ to give oxirane 101.

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Scheme 33: The aziridination of E-1b through nitrene addition.

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Review

Published 24 Oct 2017

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Dimerization reactions of aryl selenophen-2-yl-substituted thiocarbonyl S-methanides as diradical processes: a computational study

Michael L. McKee,
Grzegorz Mlostoń,
Katarzyna Urbaniak and
Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 410–416, doi:10.3762/bjoc.13.44

case of similar thiocarbonyl S-isopropanides, the intermediate zwitterions, formed in the course of the attempted [3 + 2]-cycloaddition with electron-deficient ethenes, undergo 1,3-electrocyclization yielding mixtures of stereoisomeric cyclopropanes in addition to the expected 5-membered thiolanes

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Graphical Abstract

Scheme 1: Generation and typical reactions of the reactive dialkyl and diaryl thiocarbonyl S-methanides 1.

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Figure 1: Structures of the reactive intermediates as a diradical 6 or a zwitterion 7 in the course of the di...

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Scheme 2: The in situ generation of phenyl selenophen-2-yl S-methanide (8) and its competitive reactions: 1,3...

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Figure 2: Potential 1,3-dipolar electrocyclization of thiocabonyl S-methanide 8A. Computed enthalpies (free e...

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Figure 3: Stepwise radical dimerization of the reactive thiocarbonyl S-methanide 8. Computed enthalpies (free...

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Figure 4: Potential competitive cyclization reactions of the intermediate diradical 12.

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Figure 5: a) Spin densities in the conformers 12F and 12G of diradical 12. b) Heteroatom effect on the magnit...

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Full Research Paper

Published 03 Mar 2017

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