Polyfluoroalkylation of sulfides, phosphines, and stibines by phenylpolyfluoroalkyliodonium fluoroborates
The reaction of phenyl-1,1-dihydropolyfluoroalkyliodonium fluoroborates with triphenylphosphine, triphenylstibine, dimethyl sulfide, and p-chlorophenyl methyl sulfide gave the corresponding onium salts with the polyfluoroalkyl radical at the heteroatom.Phenylperfluorohexyliodonium fluoroborate reacts with tri(dimethylamino)phosphine with the formation of perfluorohexyltri(dimethylamino)phosphonium fluoroborate.
Mironova, A. A.,Maletina, I. I.,Orda, V. V.,Yagupol'skii, L. M.
p. 469 - 472
(2007/10/02)
The Generation and Electrophilic Reactions of Dimethyl Sulphide Cation Radicals
In anhydrous methylene chloride, nitrosonium tetrafluoroborate and dimethyl sulphide reacted to give a fairly stable red-brown solution at -70 deg C which slowly decomposed at ca. -20 deg C to afford trimethylsulphonium tetrafluoroborate.The red-brown solution reacted with olefins to afford 2-nitrosoalkyldimethylsulphonium salts and/or 1,2-bis-sulphonium salts, and with anisole to give p-methoxyphenyldimethylsulphonium salt.The reactions were interpreted as involving the electrophilic dimethyl sulphide cation radical as a reactive intermediate leading the attack on the ?-bond systems.This is followed by radical combination or electron transfer-elimination to complete the addition and substitution pathways.
Chow, Yuan L.,Iwai, Kiyoshi
p. 931 - 936
(2007/10/02)
REARRANGEMENT OF BIS(ONIO)BENZOYLMETHYLIDE SALTS
The rearrangements of bis(onio)benzoylmethylide salts (ylide salts) on heating were investigated.It was established that migration of the methyl group to the oxygen occurs and that migration of the phenyl group to the oxygen only occurs in the case of triphenylphosphoniodiphenylselenoniobenzoylmethylide fluoroborate.Thermolysis of bisdimethylsulfoniobenzoylmethylide fluoroborate leads to the formation of trimethylsulfonium fluoroborate and 1,2-di(methylthio)-1,2-dibenzoylethylene.