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2005
Organo-phosphorus compounds
S 0080
Phosphonates Containing Sulfur and Selenium. Synthesis of Vinylphosphonates
α-Sulfenyl, α-Selenenyl, α-Sulfinyl and α-Seleninyl Moieties and Studies
14- 181 Bearing
on Nucleophilic Addition. — Vinylphosphonates bearing an α sulfoxide group are
found to undergo nucleophilic addition with high facial stereoselectivity. However,
epimerization at the α-C atom takes place leading to diastereomeric product mixtures.
Starting from selenide derivatives high diastereoselectivity can be obtained. Vinylphosphonates with a selenoxide group easily undergo selenoxide elimination giving various
unsaturated phosphonates in the presence of nucleophiles. In the absence of nucleophiles convenient formation of phosphorylalkynes is observed. — (MIDURA*, W. H.;
KRYSIAK, J. A.; Tetrahedron 60 (2004) 52, 12217-12229; Dep. Heteroorg. Chem.,
Pol. Acad. Sci., PL-90-363 Lodz, Pol.; Eng.) — Jannicke
2005
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