Bildung von Nitronsäuren durch Ringöffnung von Nitrocyclopropanen über einen konzertierten, säurekatalysierten Mechanismus

Cao, Weiguo; Erden, İhsan; Keeffe, James R.

doi:10.1002/ange.19951071016

Angewandte Chemie

1995

DOI: 10.1002/ange.19951071016

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Bildung von Nitronsäuren durch Ringöffnung von Nitrocyclopropanen über einen konzertierten, säurekatalysierten Mechanismus

Weiguo Cao

İhsan Erden

James R. Keeffe

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Cited by 2 publications

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“…The process is also favoured by the relief of ring strain, which explains why such nitrocyclopropanes are significantly more basic than expected. 262Scheme 114.Ring-opening addition of trifluoroacetic acid (TFA) onto well-chosen nitrocyclopropanes 262. …”

mentioning

confidence: 99%

Ring-opening, cycloaddition and rearrangement reactions of nitrogen-substituted cyclopropane derivatives

Rassadin

Six

2016

Tetrahedron

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mentioning

confidence: 99%

Ring-opening, cycloaddition and rearrangement reactions of nitrogen-substituted cyclopropane derivatives

Rassadin

Six

2016

Tetrahedron

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Conjugate Addition versus Cycloaddition/Condensation of Nitro Compounds in Water: Selectivity, Acid–Base Catalysis, and Induction Period

Guideri

Sarlo

Machetti

2012

Chemistry A European J

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Nitroacetates and nitroacetamides react in water as in chloroform with electron‐deficient dipolarophiles to give condensation or conjugate addition products under base catalysis. In general, high selectivity towards condensation is observed in water, with shorter induction periods than in chloroform. In water, condensations slowly occur even without base; kinetic profiles evidence the catalytic effect of the base, which should be related to the conversion into the tautomer nitronic acid. Condensations in water provide convenient access to isoxazole derivatives bearing various functional groups including ammonium, carboxy, and carboxyamide.

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Bildung von Nitronsäuren durch Ringöffnung von Nitrocyclopropanen über einen konzertierten, säurekatalysierten Mechanismus

Cited by 2 publications

References 27 publications

Ring-opening, cycloaddition and rearrangement reactions of nitrogen-substituted cyclopropane derivatives

Ring-opening, cycloaddition and rearrangement reactions of nitrogen-substituted cyclopropane derivatives

Conjugate Addition versus Cycloaddition/Condensation of Nitro Compounds in Water: Selectivity, Acid–Base Catalysis, and Induction Period

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