Matches in SemOpenAlex for { <https://semopenalex.org/work/W2010793670> ?p ?o ?g. }
- W2010793670 endingPage "1107" @default.
- W2010793670 startingPage "1101" @default.
- W2010793670 abstract "Enolate können mit Carbonylverbindungen nach einem polaren Mechanismus oder einem Mechanismus mit SET (single-electron transfer)-Teilschritten reagieren. Die Umsetzungen von Lithium-8-(dimethylamino)heptafulven-8-olat (1) mit Iodmethan und mit den Carbonylverbindungen Benzaldehyd (2a), Benzophenon (2b), Phenylglyoxylsäure-methylester (2c), Benzil (2d) und 4-Nitrobenzaldehyd (2e) werden unter diesem Gesichtspunkt untersucht. Die Struktur und die Verteilung der aus konkurrierenden Reaktionsabläufen entstehenden Verbindungen dienen der mechanistischen Diskussion. Die Chemoselektion führt entweder zur oxidativen Dimerisierung des Heptafulvens 1 bzw. Reduktion der jeweiligen Carbonylverbindung oder zur „aldolartigen”︁ CC-Verknüpfung. Beide Reaktionswege enden bei Gemischen stereoisomerer und regioisomerer Verbindungen. Die Beteiligung von Einelektronübertragungsschritten folgt zweifelsfrei aus der Produktzusammensetzung. Eine Korrelation zwischen dem Reduktionspotential der Carbonylverbindungen und dem Produktspektrum wird gefunden. Charge Separation on Molecular Basis: Chemoselectivity, Regio-, and Stereoselectivity of CC Bond Formation as Probes for Electron-Transfer Processes Lithium 8-(dimethylamino)heptafulven-8-olate (1), containing the cross-conjugated heptafulvene structural unit, was investigated with respect to SET (single-electron transfer)-type and polar mechanisms in reactions with methyl iodide and with the carbonyl compounds benzaldehyde (2a), benzophenone (2b), methyl phenylglyoxylate (2c), benzil (2d), and 4-nitrobenzaldehyde (2e). The selectivity of product formation was used as a mechanistic probe. Experimentally, two reaction pathways with different chemoselectivity were observed: Oxidative dimerisation of the heptafulvene 1 accompanied by reduction of the carbonyl compound and “aldol-type” reactions. The specific outcome depends on the electronic properties of the carbonyl compounds. A qualitative correlation between the reduction potentials of the carbonyl compounds and the products formed has been found." @default.
- W2010793670 created "2016-06-24" @default.
- W2010793670 creator A5011761211 @default.
- W2010793670 creator A5033302828 @default.
- W2010793670 creator A5040124015 @default.
- W2010793670 creator A5042264389 @default.
- W2010793670 creator A5044729757 @default.
- W2010793670 date "1988-06-01" @default.
- W2010793670 modified "2023-10-14" @default.
- W2010793670 title "Ladungstrennung auf molekularer Basis: Chemoselektivität, Regio- und Stereoselektivität der CC-Verknüpfung als Sonden für Elektronentransfer-Prozesse" @default.
- W2010793670 cites W1973249715 @default.
- W2010793670 cites W1976468175 @default.
- W2010793670 cites W1982953683 @default.
- W2010793670 cites W1989928446 @default.
- W2010793670 cites W2016298670 @default.
- W2010793670 cites W2017545638 @default.
- W2010793670 cites W2023959266 @default.
- W2010793670 cites W2025309803 @default.
- W2010793670 cites W2030769296 @default.
- W2010793670 cites W2045518428 @default.
- W2010793670 cites W2047431470 @default.
- W2010793670 cites W2048118129 @default.
- W2010793670 cites W2048227564 @default.
- W2010793670 cites W2050278283 @default.
- W2010793670 cites W2054129058 @default.
- W2010793670 cites W2062215916 @default.
- W2010793670 cites W2070726228 @default.
- W2010793670 cites W2072628997 @default.
- W2010793670 cites W2073905646 @default.
- W2010793670 cites W2075444248 @default.
- W2010793670 cites W2085499647 @default.
- W2010793670 cites W2091359125 @default.
- W2010793670 cites W2111575679 @default.
- W2010793670 cites W2123608977 @default.
- W2010793670 cites W2161763157 @default.
- W2010793670 cites W2167860920 @default.
- W2010793670 cites W2326192528 @default.
- W2010793670 cites W2952049739 @default.
- W2010793670 cites W2952257556 @default.
- W2010793670 cites W4213028363 @default.
- W2010793670 cites W4214694974 @default.
- W2010793670 cites W4250100852 @default.
- W2010793670 cites W66721052 @default.
- W2010793670 doi "https://doi.org/10.1002/cber.19881210613" @default.
- W2010793670 hasPublicationYear "1988" @default.
- W2010793670 type Work @default.
- W2010793670 sameAs 2010793670 @default.
- W2010793670 citedByCount "3" @default.
- W2010793670 crossrefType "journal-article" @default.
- W2010793670 hasAuthorship W2010793670A5011761211 @default.
- W2010793670 hasAuthorship W2010793670A5033302828 @default.
- W2010793670 hasAuthorship W2010793670A5040124015 @default.
- W2010793670 hasAuthorship W2010793670A5042264389 @default.
- W2010793670 hasAuthorship W2010793670A5044729757 @default.
- W2010793670 hasConcept C134018914 @default.
- W2010793670 hasConcept C155647269 @default.
- W2010793670 hasConcept C161790260 @default.
- W2010793670 hasConcept C178790620 @default.
- W2010793670 hasConcept C181647583 @default.
- W2010793670 hasConcept C185592680 @default.
- W2010793670 hasConcept C188027245 @default.
- W2010793670 hasConcept C2776211377 @default.
- W2010793670 hasConcept C2776455741 @default.
- W2010793670 hasConcept C2777768854 @default.
- W2010793670 hasConcept C2778279444 @default.
- W2010793670 hasConcept C2778541603 @default.
- W2010793670 hasConcept C2778870691 @default.
- W2010793670 hasConcept C2779692420 @default.
- W2010793670 hasConcept C2779825165 @default.
- W2010793670 hasConcept C2780450521 @default.
- W2010793670 hasConcept C521977710 @default.
- W2010793670 hasConcept C68381374 @default.
- W2010793670 hasConcept C71240020 @default.
- W2010793670 hasConcept C71924100 @default.
- W2010793670 hasConceptScore W2010793670C134018914 @default.
- W2010793670 hasConceptScore W2010793670C155647269 @default.
- W2010793670 hasConceptScore W2010793670C161790260 @default.
- W2010793670 hasConceptScore W2010793670C178790620 @default.
- W2010793670 hasConceptScore W2010793670C181647583 @default.
- W2010793670 hasConceptScore W2010793670C185592680 @default.
- W2010793670 hasConceptScore W2010793670C188027245 @default.
- W2010793670 hasConceptScore W2010793670C2776211377 @default.
- W2010793670 hasConceptScore W2010793670C2776455741 @default.
- W2010793670 hasConceptScore W2010793670C2777768854 @default.
- W2010793670 hasConceptScore W2010793670C2778279444 @default.
- W2010793670 hasConceptScore W2010793670C2778541603 @default.
- W2010793670 hasConceptScore W2010793670C2778870691 @default.
- W2010793670 hasConceptScore W2010793670C2779692420 @default.
- W2010793670 hasConceptScore W2010793670C2779825165 @default.
- W2010793670 hasConceptScore W2010793670C2780450521 @default.
- W2010793670 hasConceptScore W2010793670C521977710 @default.
- W2010793670 hasConceptScore W2010793670C68381374 @default.
- W2010793670 hasConceptScore W2010793670C71240020 @default.
- W2010793670 hasConceptScore W2010793670C71924100 @default.
- W2010793670 hasIssue "6" @default.
- W2010793670 hasLocation W20107936701 @default.
- W2010793670 hasOpenAccess W2010793670 @default.
- W2010793670 hasPrimaryLocation W20107936701 @default.