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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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