Generation of nitroalkanes, hydroximoyl halides and nitrile oxides from the reactions of β-nitrostyrenes with Grignard or organolithium reagents

Ching Fa Yao*, Kuo Hsi Kao, Ju Tsung Liu, Cheng Ming Chu, Yeh Wang, Wen Chang Chen, Yu Mei Lin, Wen Wei Lin, Ming Chung Yan, Jing Yuan Liu, Ming Ching Chuang, Jin Lien Shiue

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

50 引文 斯高帕斯(Scopus)

摘要

The β-nitrostyrenes 1 or 2 react with Grignard or organolithium reagents in ether or THF solution to generate by 1,4-addition the intermediate nitronates A. When A is treated with dilute hydrochloric acid, high yields of the nitroalkanes 3 (and oximes 4) or 5 are obtained Hydroximoyl halides 6, 8 or nitrile oxides 7 can be isolated when the intermediate A is slowly added to the ice cold concentrated hydrohalic acid. The same products 6 and/or 7 are observed if the nitronates, generated from the substrate 1a, are added to 85% aqueous H2SO4 but only the hydrolyzed carboxylic acids 9 are generated when the β-nitrostyrenes 2 are reacted with Grignard reagents and worked up under the same condition. The nitrile oxides 7 can undergo 1,3-dipolar cycloaddition with alkenes or alkynes to generate 2-isoxazolines or isoxazoles. A one-pot synthesis of the [n,3,0] bicyclic (n = 3 or 4) compounds 23-27 by intramolecular nitrile oxide-olefin cycloadditions is reported.

原文英語
頁(從 - 到)791-822
頁數32
期刊Tetrahedron
54
發行號5-6
DOIs
出版狀態已發佈 - 1998 一月 29

ASJC Scopus subject areas

  • 生物化學
  • 藥物發現
  • 有機化學

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