https://scholars.lib.ntu.edu.tw/handle/123456789/625162
標題: | Generation of nitroalkanes, hydroximoyl halides and nitrile oxides from the reactions of β-nitrostyrenes with Grignard or organolithium reagents | 作者: | Yao C.-F Kao K.-H Liu J.-T Chu C.-M Wang Y WEN-CHANG CHEN Lin Y.-M Lin W.-W Yan M.-C Liu J.-Y Chuang M.-C Shiue J.-L. |
公開日期: | 1998 | 卷: | 54 | 期: | 44687 | 起(迄)頁: | 791-822 | 來源出版物: | Tetrahedron | 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. |
URI: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-0032576787&doi=10.1016%2fS0040-4020%2897%2910356-8&partnerID=40&md5=fff987271570ded965dac3f827b3f223 https://scholars.lib.ntu.edu.tw/handle/123456789/625162 |
ISSN: | 00404020 | DOI: | 10.1016/S0040-4020(97)10356-8 | SDG/關鍵字: | halide; nitrile; nitroalkane; organolithium compound; styrene derivative; article; electron transport; hydrolysis; nuclear magnetic resonance; priority journal; reaction analysis; synthesis |
顯示於: | 化學工程學系 |
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