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• W2034304448 abstract "Die Decarboxylierungsgeschwindigkeit der von Pyridin, Chinolin und Isochinolin abgeleiteten N-Methyl-carbonsäurebetaine hängt stark von deren Solvatation ab. Die Betaine 8-12 mit der Carboxylat-Gruppe in α-Stellung zum quartären Stickstoff decarboxylieren in aprotischen Lösungsmitteln bereits bei 60° (Tab. 2). Die dabei primär entstehenden reaktiven Zwischenstufen (Ylide vom Typ 2) lassen sich durch elektrophile Reagenzien wie Diazonium-Ionen (13a), Diazo-Verbindungen (13b,f–h), Azide (13c–e) und Benzaldehyd abfangen (Schemata 1 und 2). Damit wird die α-Stellung quartärer Sechsring-Heterocyclen unter milden Bedingungen elektrophilen Substitutionen zugänglich. Der Vergleich der relativen Bildungstendenz der Ylide mit der kinetischen Acidität analoger aromatischer Verbindungen zeigt, daß auch bei den Yliden 2 ein induktiver, elektrostatischer Effekt die Stabilität bestimmt. Heterocyclic Ylides, II1). Ylides via Decarboxylation of N-Methylcarboxylates Derived from Pyridine, Quinoline, and Isoquinoline The rate of decarboxylation of N-methylcarboxylates derived from pyridine, quinoline, and isoquinoline strongly depends on solvation. In aprotic solvents the zwitterions 8-12 having the carboxylate group in the α-position to the quaternary nitrogen readily lose carbon dioxide at 60° (Table 2). The reactive intermediates (ylides of type 2) initially formed, can be trapped by electrophilic reagents (charts 1 and 2) such as diazonium ions (13a), diazo compounds (13b,f-h), azides (13c-e), and benzaldehyde. Thus the α-position of quaternary six membered heterocycles is susceptible to electrophilic substitution under mild conditions. Comparison of the relative tendency of ylide formation with the kinetic acidity of analogous aromatic compounds, reveals that in the case of the ylides 2 as well, an inductive electrostatic effect determines the stability." @default.
• W2034304448 created "2016-06-24" @default.
• W2034304448 creator A5016921888 @default.
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• W2034304448 date "1970-03-16" @default.
• W2034304448 modified "2023-10-16" @default.
• W2034304448 title "Heterocyclische Ylide, II1) Ylide durch Decarboxylierung vonN-Methyl-carbonsäurebetainen des Pyridins, Chinolins und Isochinolins" @default.
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• W2034304448 doi "https://doi.org/10.1002/jlac.19707320105" @default.
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