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N,N′-Bis(trimethylsilylmethyl)thiocarbamide and N,N′-Bis(trimethylsilylmethyl)-λ6-thiocarbamide S,S-Dioxide

“…CH 2 CH 2 NH] 2 fragment [133], is fairly easy oxidized without side processes. However, dioxide IV is a less active reducing agent than its silicon-containing g-analog [1]. The latter reduces Mn +7 within 10330 min at any pH of the medium.…”

“…The IR spectrum of compound IV has no absorption band in the range 169531660 cm !1 , characteristic of n(C=N), which distinguishes it from the spectra of previously prepared organosilicon thiocarbamide S,Sdioxides [1,3]. In this connection compound IV can not be regarded as an organosilicon derivative of formamidinesulfinic acid Me 3 SiCH 2 NHC(SOOH)= NCH 2 SiMe 3 .…”

“…We previously reported the first synthesis of organosilicon derivatives of thiocarbamide dioxide [X 3 SiCH 2 CH 2 CH 2 NH] 2 CSO 2 , X 3 Si = (C 2 H 5 ) 3 Si, N(CH 2 CH 2 O) 3 Si, and O 1.5 Si] [133]. With the purpose of preparing analogs of the general formula [X 3 Si .…”

“…With the purpose of preparing analogs of the general formula [X 3 Si . CH 2 NH]CSO 2 , we have synthesized formerly unknown N,N`-bis(trimethylsilylmethyl)thiocarbamide (I) and studied its oxidation to N,N`-Bis(trimethylsilylmethyl)-l 6 -thiocarbamide S,S-dioxide.…”

“…It easily decomposes when heated above 160oC to form compound II and (isothiocyanatomethyl)trimethylsilane (III). Thiocarbamide I, like its analog N,N`-bis- [3-(triethylsilyl)propyl]thiocarbamide [1], is easily oxidized with 50% hydrogen peroxide in dioxane at (-5)-0oC to give N,N`-bis(trimethylsilylmethyl)-l 6 -thiocarbamide S,S-dioxide (IV) as a white solid (mp 1973 199oC) almost insoluble in organic solvents and readily soluble in water.…”