Conformational analysis of 1-oxaspiro[5.5]undecanes. A powerful probe for theendoand theexoanomeric effects in acetals
作者:
Pierre Deslongchamps,
Normand Pothier,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1990)
卷期:
Volume 68,
issue 4
页码: 597-603
ISSN:0008-4042
年代: 1990
DOI:10.1139/v90-092
出版商: NRC Research Press
数据来源: NRC
摘要:
A13C nuclear magnetic resonance spectroscopy study of 1-oxaspiro[5.5]undecanes1,4, and5as a function of temperature is reported. Compound1exists as a rapidly equilibrating mixture of a major and a minor conformer (1aand1b) at room temperature that can be observed at low temperature. By comparison, 1,7-dioxaspiro[5.5]undecane2is conformationally rigid in a single conformation (2a) at room temperature. This completely different behavior demonstrates the importance of theendoand theexoanomeric effects in the acetal function.Keywords: spiro ethers, conformational analysis,13C NMR.
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