142778-06-1Relevant articles and documents
Synthesis of cyclopropane-containing phosphorus compounds by radical coupling of butenylindium with iodo phosphorus compounds
Kiyokawa, Kensuke,Suzuki, Itaru,Yasuda, Makoto,Baba, Akio
supporting information; experimental part, p. 2163 - 2171 (2011/05/16)
The radical coupling of α- or β-iodo phosphorus compounds such as iodo phosphonate, iodo phosphane oxide, and iodo phosphonothioate with butenylindium species, prepared by transmetalation between a (cyclopropylmethyl)stannane and InBr3, afforded the corresponding cyclopropylmethylated products. The radical reaction was initiated by the radical species generated from butenylindium assisted by a small amount of oxygen. Butenylindium works not only as a cyclopropylmethylating reagent, but also as a radical initiator. For successful coupling, a tin/indium transmetalation was used, where it was important for the tin halide by-product to be inert to the reaction system. In addition, the transmetalation of a (cyclopropylmethyl)stannane and InBr3 provided the dibutenylindium bromide as a single product, which smoothly coupled with the unstable phosphonyl radical species from the iodo phosphorus compound. A photochemical method (UV irradiation) was also applied and accelerated the coupling reaction. The cyclopropylmethylated phosphonate produced was a good intermediate in the Horner-Wadsworth-Emmons reaction and gave functionalized olefins bearing the cyclopropane moiety. Copyright
Metallo-phosphorylation of olefins: Reaction of diethyl chlorophosphate with Zirconocene-ethylene complex
Xi,Ma,Li
, p. 2554 - 2555 (2007/10/03)
Zirconocene-ethylene complex Cp2Zr (CH2 = CH2) reacted with chlorophosphate to form zircono-ethylphosphonate, which could be converted into various functionalized ethylphosphonates.
