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- Wieland-Gumlich_aldehyde abstract "The so-called Wieland-Gumlich aldehyde (6) is an indoline derived by chemical degradation from strychnine. This compound is of some commercial interest as a chemical intermediate. It was first synthesized in 4 steps from strychnine (1) by Walter Gumlich and Koozoo Kaziro working in the laboratory of Heinrich Wieland. This degradation study was part of an attempt to elucidate the chemical structure of strychnine.This degradation takes place through conversion of strychnine to the oxime 2 using amyl nitrite, Beckmann fragmentation of 2 to the carbamic acid 3 by use of thionyl chloride, decarboxylation of 3 to nitrile 4, and nucleophilic displacement of cyanide by barium hydroxide to give hemiacetal 5, which is in equilibrium with the Wieland-Gumlich aldehyde (6).The Wieland-Gumlich aldehyde synthesisThe Wieland-Gumlich aldehyde reverts to strychnine in a single reaction using malonic acid, acetic anhydride and sodium acetate in acetic acid.The Wieland-Gumlich aldehyde has been used in the industrial synthesis of alcuronium chloride (Alloferin) via dimerization.".
- Wieland-Gumlich_aldehyde thumbnail Wieland-Gumlich_aldehyde.svg?width=300.
- Wieland-Gumlich_aldehyde wikiPageID "23973040".
- Wieland-Gumlich_aldehyde wikiPageLength "3319".
- Wieland-Gumlich_aldehyde wikiPageOutDegree "25".
- Wieland-Gumlich_aldehyde wikiPageRevisionID "666846688".
- Wieland-Gumlich_aldehyde wikiPageWikiLink Acetic_acid.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Acetic_anhydride.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Alcuronium_chloride.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Amyl_nitrite.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Barium_hydroxide.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Beckmann_fragmentation.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Beckmann_rearrangement.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Carbamic_acid.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Category:Aldehydes.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Category:Indoles.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Cyanide.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Decarboxylation.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Dimer_(chemistry).
- Wieland-Gumlich_aldehyde wikiPageWikiLink Dimerization_(chemistry).
- Wieland-Gumlich_aldehyde wikiPageWikiLink Heinrich_Otto_Wieland.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Hemiacetal.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Indoline.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Malonic_acid.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Nitrile.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Nucleophilic_displacement.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Nucleophilic_substitution.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Oxime.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Sodium_acetate.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Strychnine.
- Wieland-Gumlich_aldehyde wikiPageWikiLink Thionyl_chloride.
- Wieland-Gumlich_aldehyde wikiPageWikiLink File:Wieland-Gumlich_aldehyde_synthesis.svg.
- Wieland-Gumlich_aldehyde wikiPageWikiLinkText "Wieland-Gumlich aldehyde".
- Wieland-Gumlich_aldehyde hasPhotoCollection Wieland-Gumlich_aldehyde.
- Wieland-Gumlich_aldehyde imagefile "Wieland-Gumlich aldehyde.svg".
- Wieland-Gumlich_aldehyde imagesize "200".
- Wieland-Gumlich_aldehyde othernames "Caracurine VII, Deacetyldiaboline".
- Wieland-Gumlich_aldehyde wikiPageUsesTemplate Template:Chembox.
- Wieland-Gumlich_aldehyde wikiPageUsesTemplate Template:Reflist.
- Wieland-Gumlich_aldehyde subject Category:Aldehydes.
- Wieland-Gumlich_aldehyde subject Category:Indoles.
- Wieland-Gumlich_aldehyde hypernym Indoline.
- Wieland-Gumlich_aldehyde type Article.
- Wieland-Gumlich_aldehyde type ChemicalCompound.
- Wieland-Gumlich_aldehyde type ChemicalSubstance.
- Wieland-Gumlich_aldehyde type Aldehyde.
- Wieland-Gumlich_aldehyde type Article.
- Wieland-Gumlich_aldehyde type Chemical.
- Wieland-Gumlich_aldehyde type Heterocycle.
- Wieland-Gumlich_aldehyde type ChemicalObject.
- Wieland-Gumlich_aldehyde type Thing.
- Wieland-Gumlich_aldehyde type Q11173.
- Wieland-Gumlich_aldehyde comment "The so-called Wieland-Gumlich aldehyde (6) is an indoline derived by chemical degradation from strychnine. This compound is of some commercial interest as a chemical intermediate. It was first synthesized in 4 steps from strychnine (1) by Walter Gumlich and Koozoo Kaziro working in the laboratory of Heinrich Wieland.".
- Wieland-Gumlich_aldehyde label "Wieland-Gumlich aldehyde".
- Wieland-Gumlich_aldehyde sameAs m.076xfp9.
- Wieland-Gumlich_aldehyde sameAs Vieland-Gumlih_aldehid.
- Wieland-Gumlich_aldehyde sameAs Vieland-Gumlih_aldehid.
- Wieland-Gumlich_aldehyde sameAs Q7998928.
- Wieland-Gumlich_aldehyde sameAs Q7998928.
- Wieland-Gumlich_aldehyde wasDerivedFrom Wieland-Gumlich_aldehyde?oldid=666846688.
- Wieland-Gumlich_aldehyde depiction Wieland-Gumlich_aldehyde.svg.
- Wieland-Gumlich_aldehyde isPrimaryTopicOf Wieland-Gumlich_aldehyde.