Yao, Ching-FaChing-FaYaoKao, Kuo-HsiKuo-HsiKaoLiu, Ju-TsungJu-TsungLiuChu, Cheng-MingCheng-MingChuWang, YehYehWangWEN-CHANG CHENLin, Yu-MeiYu-MeiLinLin, Wen-WeiWen-WeiLinYan, Ming-ChungMing-ChungYanLiu, Jing-YuanJing-YuanLiuChuang, Ming-ChingMing-ChingChuangShiue, Jin-LienJin-LienShiue2022-11-162022-11-16199800404020https://www.scopus.com/inward/record.uri?eid=2-s2.0-0032576787&doi=10.1016%2fS0040-4020%2897%2910356-8&partnerID=40&md5=fff987271570ded965dac3f827b3f223https://scholars.lib.ntu.edu.tw/handle/123456789/625162The 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.[SDGs]SDG6halide; nitrile; nitroalkane; organolithium compound; styrene derivative; article; electron transport; hydrolysis; nuclear magnetic resonance; priority journal; reaction analysis; synthesisjournal article10.1016/S0040-4020(97)10356-82-s2.0-0032576787