Rhodium-Catalyzed Regio- and Stereoselective 1-Seleno-2-thiolation of 1-Alkynes
Rhodium complex RhH(PPh3)4 and 1,1′-bis(diphenylphosphino)ferrocene catalyze the regio- and stereoselective additions of diaryl disulfides and diaryl diselenides to 1-alkynes giving (Z)-1-arylseleno-2-arylthio-1-alkenes. The catalyst promotes the addition reaction of dibutyl disulfide and dibutyl diselenide to 1-octyne with a similar selectivity giving (Z)-1-butylseleno-2-butylthio-1-octene but with a lower catalytic activity. The same product is obtained with a higher yield, when excess dibutyl disulfide is used against dibutyl diselenide in the presence of RhH(PPh3)4 and 1,4-diphenylphosphinobutane.
Synthesis of Vinyl Selenides or Sulfides and Ketene Selenoacetals or Thioacetals by Nickel(II) Vinylation of Sodium Benzeneselenolate or Benzenethiolate
The substitution of bromine atom on a double bond by benzeneselenolate or benzenethiolate anions is catalyzed by the bis(pyridine)nickel bromide complex.Various alkenyl selenides or sulfides and seleno- or thio acetals are prepared in good to excellent yi
Cristau, H. J.,Chabaud, B.,Labaudiniere, R.,Christol, H.
p. 875 - 878
(2007/10/02)
NEW SYNTHESIS OF VINYL SELENIDES NUCLEOPHILIC SUBSTITUTIONS OF UNACTIVATED VINYL HALIDES BY SELENIDE ANIONS
Alkyl and aryl selenide anions react with unactivated vinyl halides, in dipolar aprotic solvents, to give alkyl or aryl vinyl selenides in good yields.These reactions are stereospecific and occur with retention of configuration.
Tiecco, M.,Testaferri, L.,Tingoli, M.,Chianelli, D.,Montanucci, M.
p. 4975 - 4978
(2007/10/02)
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