Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
J Am Chem Soc. 2013 Mar 6;135(9):3355-8. doi: 10.1021/ja311942e. Epub 2013 Feb 22.
Nitroolefin is a common and versatile reagent. Its synthesis from olefin is generally limited by the formation of mixture of cis and trans compounds. Here we report that silver nitrite (AgNO2) along with TEMPO can promote the regio- and stereoselective nitration of a broad range of olefins. This work discloses a new and efficient approach wherein starting from olefin, nitroalkane radical formation and subsequent transformations lead to the desired nitroolefin in a stereoselective manner.
硝烯是一种常见且用途广泛的试剂。其通常由烯烃合成,但会形成顺式和反式混合物。在此,我们报告了亚硝酸银(AgNO2)与 TEMPO 可以促进广泛的烯烃的区域和立体选择性硝化。该工作揭示了一种新的有效方法,通过该方法,从烯烃出发,硝烷自由基的形成和随后的转化以立体选择性的方式生成所需的硝烯。