168129-74-6Relevant academic research and scientific papers
Studies on the Free Radical Carbon-Carbon Bond Formation in the Reaction of α-Phosphoryl Sulfides and Selenides with Alkenes
Balczewski, Piotr,Pietrzykowski, Witold M.,Mikolajczyk, Marian
, p. 7727 - 7740 (1995)
α-Mono- and α,α-disubstituted α-phosphoryl radicals 9 were generated from the easy accessible α-phosphoryl sulfides 4, 5 and α-phosphoryl selenides 11, 12 and reacted with the electron rich alkenes 6 under the reductive (n-Bu3SnH/AIBN) conditions to give the functionalized phosphonates 7 in 32+68percent yield.Two fragmentation processes of the phosphonate α-alkoxy alkyl radicals are also described. - Key words: α-phosphoryl sulfides, α-phosphoryl selenides, intermolecular radical reaction, radical fragmentation, phosphonates, tri-n-butyltin hydride, α,α'-azaisobutyronitrile
Free radical desulfenylation and deselenylation of α-sulfur and α-seleno substituted phosphonates with the n-Bu3SnH/AIBN reagents system.
Balczewski,Piotr
, p. 113 - 122 (2007/10/03)
Selestive desulfenylation and deselenylation of α-sulfur- and α-seleno-substituted phosphonates under free radical condition are described.Chemoselectivity and scope of title reaction were studied using phosphonates additionaly functionalized in the α-position alkyl, phenyl,ethoxy,chloro,carbonyl and sulfenyl groups.It was found the reduction of a halogen tolerates the presence of the sulfenyl group and the latter could be reduced in the presence of the sulfinyl and sulfonyl moieties.Moreover,one sulfenyl group was selectively removed from α-phosphoryl dithioacetals and the phenylsulphenyl group was reduced preferentially in the presence of the methylsulfenyl one. Key words:Desulfenylation,deselenylation,α-phosphoryl sulfides,α-phosphoryl selenides, tri-n-butyltinhydride,α,α-azaisobutyronitrile.
