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Relative acidities and structure analysis of cis and trans isomers of 1,5-oxazaspiro[5.5] undecane derivatives by multinuclear magnetic resonance

, : Relative acidities and structure analysis of cis and trans isomers of 1,5-oxazaspiro[5.5] undecane derivatives by multinuclear magnetic resonance. Magnetic Resonance in Chemistry 48(5): 356-361

The relative acidities of the cis and trans isomers of a series of 1,5-oxazaspiro[5.5]undecane derivatives were determined by measuring DeltapK in acid-base titrations followed by (1)H NMR. Relative structural stabilities were determined by measuring substituent chemical shift and gamma-gauche effects in (13)C, (15)N, and (17)O NMR. Crystallographic characterization of a model spiro[5.5]undecane is presented to support the basicity in solid state.


PMID: 20306516

DOI: 10.1002/mrc.2592

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