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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