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- Q904710 subject Q7458901.
- Q904710 subject Q8343673.
- Q904710 subject Q8983024.
- Q904710 abstract "The Stetter reaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst. While the related 1,2-addition reaction, the benzoin condensation, was known since the 1830s, the Stetter reaction was not reported until 1973 by Dr. Hermann Stetter. The reaction provides synthetically useful 1,4-dicarbonyl compounds and related derivatives from aldehydes and Michael acceptors. Unlike 1,3-dicarbonyls, which are easily accessed through the Claisen condensation, or 1,5-dicarbonyls, which are commonly made using a Michael reaction, 1,4-dicarbonyls are challenging substrates to synthesize, yet are valuable starting materials for several organic transformations, including the Paal–Knorr synthesis of furans and pyrroles. Traditionally utilized catalysts for the Stetter reaction are thiazolium salts and cyanide anion, but more recent work toward the asymmetric Stetter reaction has found triazolium salts to be effective. The Stetter reaction is an example of umpolung chemistry, as the inherent polarity of the aldehyde is reversed by the addition of the catalyst to the aldehyde, rendering the carbon center nucleophilic rather than electrophilic.".
- Q904710 thumbnail Stetter_reaction_general_example.png?width=300.
- Q904710 wikiPageWikiLink Q11351.
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- Q904710 wikiPageWikiLink Q2181524.
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- Q904710 wikiPageWikiLink Q7334670.
- Q904710 wikiPageWikiLink Q7458901.
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- Q904710 wikiPageWikiLink Q812563.
- Q904710 wikiPageWikiLink Q818514.
- Q904710 wikiPageWikiLink Q82264.
- Q904710 wikiPageWikiLink Q83187.
- Q904710 wikiPageWikiLink Q8343673.
- Q904710 wikiPageWikiLink Q8983024.
- Q904710 wikiPageWikiLink Q898501.
- Q904710 wikiPageWikiLink Q898628.
- Q904710 wikiPageWikiLink Q899050.
- Q904710 wikiPageWikiLink Q899736.
- Q904710 wikiPageWikiLink Q901195.
- Q904710 wikiPageWikiLink Q904718.
- Q904710 wikiPageWikiLink Q907664.
- Q904710 wikiPageWikiLink Q908086.
- Q904710 wikiPageWikiLink Q911365.
- Q904710 comment "The Stetter reaction is a reaction used in organic chemistry to form carbon-carbon bonds through a 1,4-addition reaction utilizing a nucleophilic catalyst. While the related 1,2-addition reaction, the benzoin condensation, was known since the 1830s, the Stetter reaction was not reported until 1973 by Dr. Hermann Stetter. The reaction provides synthetically useful 1,4-dicarbonyl compounds and related derivatives from aldehydes and Michael acceptors.".
- Q904710 label "Stetter reaction".
- Q904710 depiction Stetter_reaction_general_example.png.