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Conjugate Addition of Hydroxylamines to 4-Substituted Butenolides

 

作者: Irma Panfil,   Wojciech Abramski,   Marek Chmielewski,  

 

期刊: Journal of Carbohydrate Chemistry  （Taylor Available online 1998）
卷期: Volume 17, issue 9  

页码: 1395-1403

 

ISSN:0732-8303

 

年代: 1998

 

DOI:10.1080/07328309808002361

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

4-Substituted-butenolides treated with free hydroxylamine at pH=5 undergo conjugate addition - rearrangement to afford isoxazolidin-5-ones. This is in contrast to N-substituted hydroxylamines which under the same conditions produce Michael adducts only. In the presence of base, butenolides undergo racemizationviaflat tautomeric forms.

 

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