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- W1497441570 abstract "Die IR- und NMR-Spektrencis-fixierter, cyclischer β-Enaminoester vom Typ der 1-Amino-2-alkoxycarbonyl-cycloalkene-(1) werden beschrieben und eingehend diskutiert: Die IR-Spektren der unsubstituierten β-Enaminoester zeigen eindeutig,dass zwischen der 1-sta¨ndigen Aminogruppe und dem Estercarbonyl keine interne Wasserstoffbru¨cke existiert, Hingegen weisen die Spektren der N-substituierten Verbindungen auf eine Chelatbru¨cke hin, deren Sta¨rke mit steigender Kettenla¨nge des Stickstoffsubstituenten zunimmt. Die NMR-Spektren der unsubstituierten Enamine besta¨tigen das Fehlen einer Wasserstoffbru¨cke. Andererseits ko¨nnen die paramagnetisch verschobenen NH-Signale der N-substituierten Verbindungen auf eine Chelatbru¨cke zuru¨ckgefu¨hrt werden. The IR and NMR spectra ofcis-fixed cyclic β-enaminoesters of the 1-amino-2-alkoxycarbonyl-cycloalkene-(1) type are described and discussed in detail. For N-substituted β-enaminoesters characteristic absorption bands in the IR definitely prove the existence of internal H-bonding. However, the corresponding data for the unsubstituted compounds exclude an internal H-chelate between the amino group in position 1 and the estercarbonyl. The NMR spectra of the unsubstituted enamines confirm the absence of H- bonds. On the other hand the paramagnetically shifted NH signals of the N-substituted compounds can be attributed to an internal chelate. The strength of the internal H- bond is largely determined by inductive and mesomeric effects of the nitrogen-substituents as well as from the polarizability of the C=O group." @default.
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- W1497441570 date "1973-12-01" @default.
- W1497441570 modified "2023-09-27" @default.
- W1497441570 title "Konjugierte enamine—III" @default.
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- W1497441570 doi "https://doi.org/10.1016/0040-4020(73)80272-8" @default.
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