111252-22-3Relevant academic research and scientific papers
Nucleophilic cleavage of the Si-C bond in organotrifluorosilanes and diorganodifluorosilanes
Voronkov, M. G.,Chermov, N. F.,Perlova, E. M.
, p. 225 - 230 (2007/10/02)
The Si-C bond in aryltrifluorosilanes, 4-XC6H4SiF3 (X = H, CH3, Cl, Br or NO2), is readily cleaved by mercury(II) salts HgY2 (Y = Cl, Br, I, CN or OCOCH3) or HgO to form organomercurials of the type 4-XC6H4HgY or (4-XC6H4)2Hg, respectively.Electron-donating substituent X facilitate the reaction, whereas electron-withdrawing substituents make it more difficult.Mercury(II) salts and mercury(II) oxide also cleave the Si-C bond in chloromethyltrifluorosilanes, F3Si(CH3-nCln) (n = 1-3) to produce the corresponding organic mercurials containing an Hg(CH3-nCln) group.The substitution of the fluorine atom in organotrifluorosilanes by an alkyl group hinders the bond cleavage between the silicon atom and the electronegative organic substituent.The reactions studied are believed to follow a nucleophilic mechanism involving asynchronous formation of a four-centered transition state with a pentacoordinate silicon atom.
Alkylidene Transfer from Monochloroalkylmercury(II) Compounds to Aromatic Amines; Selective C-Alkylation
Barluenga, Jose,Campos, Pedro J.,Roy, Miguel A.,Asensio, Gregorio
, p. 1420 - 1426 (2007/10/02)
αα-Diarylalkane derivatives have been synthesized from monochloroalkylmercury(II) compounds in a noncarbenoid alkylidene transfer reaction which takes place selectively on the aromatic ring.A mechanism is suggested for this process.Intermediate products are prepared by alternative routes to ascertain their participation in the course of the reaction.As a consequence, two different aryl groups can be successively incorporated into the alkane molecule.
