81609-30-5Relevant articles and documents
The use of aminoiminomethanesulfinic acid (thiourea dioxide) under phase transfer conditions for generating organochalcogenate anions. Synthesis of sulfides, selenides and tellurides
Comasseto, J. V.,Lang, E. S.,Ferreira, J. Tercio B.,Simonelli, F.,Correira, V. R.
, p. 329 - 340 (2007/10/02)
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.
ALKALINE HYDROLYSIS OF DIARYL DITELLURIDES UNDER PHASE TRANSFER CONDITIONS; SYNTHESIS OF ALKYL ARYL TELLURIDES
Comasseto, J. V.,Ferreira, J. T. B.,Val, Fontanillas
, p. 261 - 266 (2007/10/02)
The disproportionation reaction of diaryl ditellurides with sodium hydroxide under phase transfer conditions at room temperature is described for the first time.The phase transfer catalyst used is 2HT-75, a trade name for a mixture of dialkyldimethylammonium chlorides.The intermediates aryl tellurolates react "in situ" with alkyl halides to give the corresponding alkyl aryl tellurides (ArTeR) in 52-72percent yield.The following compounds were prepared: Ar = C6H5, R = CH3(CH2)3CH2,(CH3)2CHCH2CH2, (CH3)2CHCH2, CH3CHBrCH2CH2, CH3(CH2)8CH2, C6H5CH2, ClCH2, C6H5CH2CH2, CH2=CHCH2, C6H5CH=CHCH2, C6H5SeCH2, ; Ar = p-CH3C6H4, R = CH3(CH2)2CH2; Ar = p-CH3OC6H4, R = CH3(CH2)2CH2; Ar = p-C2H5OC6H4, R = CH3(CH2)2CH2; Ar = 2-naphthyl, R = CH3(CH2)2CH2.