Cyclic Seleninate Esters as Catalysts for the Oxidation of Sulfides to Sulfoxides, Epoxidation of Alkenes, and Conversion of Enamines to α-Hydroxyketones
作者:Eric A. Mercier、Chris D. Smith、Masood Parvez、Thomas G. Back
DOI:10.1021/jo300313v
日期:2012.4.6
sulfides to sulfoxides, alkenes to epoxides, and enamines to α-hydroxyketones. Optimal conditions were found that minimize the overoxidation of the product sulfoxides to sulfones and the hydrolysis of epoxides to diols. In some examples such as styrene derivatives, oxidative cleavage was observed instead of epoxidation. The enamine oxidations proceed via the initial formation of dimeric 2,5-diamino-1
环状硒代酸酯用作将硫化物快速氧化为亚砜,将烯烃快速氧化为环氧化物以及将烯胺快速氧化为α-羟基酮的催化剂。发现最佳条件使产物亚砜至砜的过氧化和环氧化物至二醇的水解减至最小。在某些实例中,例如苯乙烯衍生物,观察到氧化裂解而不是环氧化。烯胺的氧化过程是通过最初形成二聚2,5-二氨基-1,4-二恶烷物质而进行的,将其原位水解为最终产物。一种这样的二聚体的结构通过X射线晶体学确认。