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Reactions of ozonides. V. Selective reduction of ozonides of 10-undecenoic acid derivatives by boranes

 

作者: D. G. M. Diaper,   W. M. J. Strachan,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1967)
卷期: Volume 45, issue 1  

页码: 33-37

 

ISSN:0008-4042

 

年代: 1967

 

DOI:10.1139/v67-007

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

Borane–amine and tetrahydrofuran–borane adducts reduce 10-undecenoic acid ozonide and derivatives to 1,10-decanediol. Insufficient reagent allows selective reduction at the ozonide function, giving 10-hydroxydecanoic acid and derivatives through aldehyde intermediates. The reagents are not as selective as sodium borohydride. Thermochemical study shows an initial reaction step involving one molecule each of substrate and borane.

 

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