80436-47-1Relevant academic research and scientific papers
ADDITION OF ELEMENTAL SELENIUM TO PHOSPHONATE CARBANIONS- A KEY STEP IN THE SYNTHESIS OF VINYLPHOSPHONATES. A NEW SYNTHETIC APPROACH TO 1,4-DICARBONYL SYSTEMS.
Mikolajczyk, Marian,Grzejszczak, Slawomir,Korbacz, Katarzyna
, p. 3097 - 3100 (1981)
A convenient synthesis of vinylphosphonates which involves addition of elemental selenium to phosphonate carbanions followed by alkylation and selenoxide elimination is described.A general approach to 1,4-dicarbonyl systems based on diethyl α-methylthiovinylphosphonate is also reported.
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
