Reaction of sulfenamides with N,N-dimethylaniline in the presence of phosphorus(v) oxochloride
Reaction of arylsulfenamides with N, N-dimethylaniline in the presence of POCl3 at room temperature affords unsymmetrical diaryl sulfide, only para-substituted N, N-dimethylanilines being formed.
Zyk,Beloglazkina,Belova
p. 180 - 181
(2007/10/03)
The use of aminoiminomethanesulfinic acid (thiourea dioxide) under phase transfer conditions for generating organochalcogenate anions. Synthesis of sulfides, selenides and tellurides
A procedure is described which allows for the in situ synthesis of arylalkyl, diaryl and dialkylchalcogenides under phase transfer conditions starting from the corresponding diorganodichalcogenides.The dichalcogenides are reduced by aminoiminomethanesulfinic acid (thiourea dioxide) in alkaline medium and catalyzed by a quaternary ammonium salt.The reduction proceeds easily for diaryl disulfides and diaryl diselenides at a sodium hydroxide concentration of 13percent; diaryl ditellurides require a 50percent sodium hydroxide solution to give the aryl tellurolate anion.The dialkyl diselenides and dialkyl ditellurides are more difficult to reduce.The intermediate arylthiolates and arylselenolates are quenched by alkyl and activated aryl halides to give the corresponding sulfides and selenides in high yield (77-97percent).The aryltellurolates react with alkyl halides giving the aryl alkyl tellurides in 81-96percent yield.The procedure could not be successfully used for the synthesis of dialkylselenides and dialkyl tellurides; low yields and mixture of products were formed.
Comasseto, J. V.,Lang, E. S.,Ferreira, J. Tercio B.,Simonelli, F.,Correira, V. R.
p. 329 - 340
(2007/10/02)
SYNTHESIS OF DIARYLSELENIDES AND DIARYLSULFIDES UNDER PHASE TRANSFER CONDITIONS
Diarylselenides and diarylsulfides are synthesized from the corresponding diaryldiselenide and diaryldisulfide by reduction with aminoiminomehanesulfinic acid, and reaction with activated aryl halides under phase transfer conditions.The reactions yields vary from good to excellent.
Ferreira, J. Tercio,Simonelli, F.,Comasseto, J. V.
p. 1335 - 1342
(2007/10/02)
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