School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, PR China.
Org Biomol Chem. 2010 Feb 7;8(3):628-31. doi: 10.1039/b914944a. Epub 2009 Dec 7.
A new combination of catalyst and co-additive has been found for aminohalogenation reaction of beta-methyl-beta-nitrostyrenes with N,N-dichloro-p-tolunesulfonamide (4-TsNCl(2)). The reaction was achieved by using MnSO(4) as the catalyst together with tolunesulfonamide to give vicinal haloamino nitroalkanes with opposite regiochemistry to that generated from other electron-deficient olefins observed previously. The reaction proceeded smoothly at room temperature under nitrogen atmosphere to give useful to good yields and excellent regio and stereoselectivity. A mechanism involving the formation of chloronium intermediate was proposed to explain the resulting regio and stereochemistry.
已发现一种新的催化剂和共添加剂组合，用于β-甲基-β-硝基苯乙烯与 N,N-二氯对甲苯磺酰胺（4-TsNCl(2)）的氨基卤化反应。该反应在 MnSO(4)作为催化剂的条件下，与甲苯磺酰胺一起使用，生成顺式卤代氨基硝基烷烃，其区域化学与以前观察到的其他缺电子烯烃生成的产物相反。反应在氮气氛围下于室温下顺利进行，得到有用的至良好的产率和优异的区域和立体选择性。提出了一种涉及氯鎓中间体形成的机制来解释所得的区域和立体化学。
