Sahu Bichismita, Gururaja Guddeangadi N, Mobin Shaikh M, Namboothiri Irishi N N
Department of Chemistry, Indian Institute of Technology, Bombay, Mumbai 400 076, India.
J Org Chem. 2009 Mar 20;74(6):2601-4. doi: 10.1021/jo802274q.
Addition of bromoform to conjugated nitroalkenes in the presence of Mg provided beta-tribromomethyl nitroalkanes in good to excellent yields and diastereoselectivity. These novel Michael adducts, formed under radical conditions, underwent elimination of HBr in the same pot under reflux to afford beta-dibromomethylenated nitroalkanes in good yield. Alternatively, a one-pot high yielding synthesis of the dibromides was possible under anionic conditions via LDA mediated addition of bromoform to nitroalkenes.
在镁存在的情况下，向共轭硝基烯烃中加入溴仿可得到产率良好至优异且具有非对映选择性的β-三溴甲基硝基烷烃。这些在自由基条件下形成的新型迈克尔加成物，在回流条件下于同一反应釜中发生HBr消除反应，以良好的产率得到β-二溴亚甲基化硝基烷烃。或者，在阴离子条件下，通过LDA介导的溴仿与硝基烯烃的加成反应，可以实现二溴化物的一锅法高产率合成。
