410. Organometallic and organometalloidal fluorine compounds. Part III. Trifluoromethyl derivatives of sulphur

Abstract

The interaction of sulphur and trifluoroiodomethane yields bistrifluoromethyl disulphide, (CF,) ,S, , carbon disulphide, thiocarbonyl fluoride, and polysulphides. The structure of bistrifluoromethyl disulphide is proved chemically and its unusual hydrolysis is considered. On irradiation in presence of mercury the disulphide yields bis (trifluoromethylthio) mercury, (CF,S) ,Hg ; irradiation in absence of mercury gives bistrifluoromethyl sulphide, (CF,) 2S.

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

“…To circumvent this instability issue, the anion was associated to a metal such as Hg II , Ag I , or Cu I . First, (CF 3 S) 2 Hg was prepared by reduction of bis(trifluoromethyl) disulfide by Hg44 or by heating carbon disulfide with HgF 2 45. Despite the fact that this reagent was known for many years to be very corrosive (skin burns by contact) and toxic (approximate lethal dose in albino rats of 130 mg kg –1 ),45 it was one of the most popular nucleophilic trifluoromethylthiolating reagents.…”

Copper-mediated oxidative trifluoromethylthiolation of unactivated terminal alkenes

“…Although the trifluoromethylthio group (SCF 3 ) has been known for more than six decades, 1 it has only recently received increasing attention. 2 Its unique properties, such as the strong electron-withdrawing effect and extremely high lipophilicity, 3 make this moiety highly important in medicinal and materials chemistry.…”

The structures of some trifluoromethyl derivatives of group 6

“…This compound was prepared by Kidd and Haszeldine, by the photolysis of perfluorodimethyl disulphide. 4 It is a gas boiling at -22" C. Six photographs were taken with the sample at -80" C. They showed ten rings extending to s = 24, where 3 = (47~/A) sin (6/2). Table 1 lists the positions of the maxima and minima and the estimated intensities.…”