169617-16-7Relevant academic research and scientific papers
α-Alkyl(aryl)sulfenyl substituted β-ketophosphonates: Synthesis, properties and reactivity
Miko?ajczyk, Marian,Ba?czewski, Piotr,Chefczyńska, Hanna,Szadowiak, Aldona
, p. 3067 - 3074 (2007/10/03)
A new synthesis of the title compounds via acylation of α-lithio-α-phosphorylalkyl sulfides is described. Two additional approaches to these compounds, although less efficient, involve: (a) sulfenylation of O-silylated dialkyl β-ketophosphonates and (b) the Arbuzov reaction of triethyl phosphite with α-chloro-α- methylthiomethyl phenyl ketone. The keto-enol tautomerism of the title compounds and reactivity of the anions derived from them with electrophilic reagents were investigated. The P(O)-olefination products obtained from electron rich aromatic aldehydes were found to undergo the acid-catalyzed desulfenylation reaction affording α,β-unsaturated ketones.
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.
