164592-27-2Relevant academic research and scientific papers
Phosphonates containing sulfur and selenium. Synthesis of vinylphosphonates bearing α-sulfenyl, α-selenenyl, α-sulfinyl and α-seleninyl moieties and studies on nucleophilic addition
Midura, Wanda H.,Krysiak, Jerzy A.
, p. 12217 - 12229 (2007/10/03)
The selenenylation of racemic and optically active α-phosphoryl sulfoxides is a key step leading efficiently to α-phosphorylvinyl sulfoxides or α-phosphorylvinyl selenides depending on the reaction conditions. Oxidation of α-phosphorylvinyl selenides and subsequent thermolysis of selenoxides afford alkynylphosphonates. Studies of the stereochemical course of nucleophilic addition to α-phosphoryl sulfoxides show high facial stereoselectivity of the reaction, however, epimerisation at the α-carbon atom leads to mixtures of diastereomers. Graphical Abstract
Phosphonates Containing Sulfur and Selenium: the First Synthesis of α-Phosphorylvinyl Selenides and Selenoxides and a New Synthetic Approach to Alkynylphosphonates
Midura, Wanda H.,Mikolajczyk, Marian
, p. 2871 - 2874 (2007/10/02)
An efficient, two-step synthesis of α-phosphorylvinyl selenides 4 from α-phosphoryl sulfoxides 1 is described which involves selenenylation reaction and subsequent thermal sulfoxide elimination.Oxidation of 4 leads to α-phosphorylvinyl selenoxides 5 which upon thermolysis afford alkynylphosphonates 6.
