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Halogenation of vinyl ketoximes. Synthesis of isoxazoles and preparation and silver ion‐promoted reactions of 4‐halo‐2‐isoxazolines

 

作者: John F. Hansen,   Yong In Kim,   Stephen E. Mccrotty,   Scott A. Strong,   Douglas E. Zimmer,  

 

期刊: Journal of Heterocyclic Chemistry  (WILEY Available online 1980)
卷期: Volume 17, issue 3  

页码: 475-479

 

ISSN:0022-152X

 

年代: 1980

 

DOI:10.1002/jhet.5570170311

 

出版商: Wiley‐Blackwell

 

数据来源: WILEY

 

摘要:

AbstractReaction of several α,β‐unsaturated ketoximes withN‐bromosuccinimide (NBS) gave isoxazoles, but yields were lower and the reaction less general than a similar transformation using iodine under basic conditions. With β,β‐disubstituted oximes, 4‐halo‐5,5‐disubstituted‐2‐isoxazolines were obtained using NBS, iodine, orN‐chlorosuccinimide. Treatment of the 4‐bromoisoxazo‐lines with silver acetate or silver nitrate caused either elimination with rearrangement to give isoxazoles or substitution at C‐4, depending upon the nature

 

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