Thiocyanogen chloride

Entries 7 to 9 involve other reagents that react by similar mechanisms. In the case of thiocyanogen chloride and thiocyanogen, the formal electrophile is [NCS]+. The presumed intermediate is a cyanothiairanium ion. The thiocyanate anion is an... 

The treatment of alkynes with the combined reagent, PhICl2/Pb(SCN)2, in dichloromethane at 0-5°C provides access to frans-bis(thiocyanato)alkenes [58]. Whether thiocyanogen, thiocyanogen chloride, or [bis(thiocyanato)-iodo]benzene is responsible for dithiocyanation of the C,C-triple bond has not been established. 

Thiocyanogen Chloride. Part IV. Reaction with aromatic hydro-... 

Several types of sulfenyl chlorides are known. Sulfur monochloride and dichloride can add to dienes forming sulfor bridges. - The most commonly used sulfenyl halides are benzenesulfenyl dilorides and methanesulfenyl chloride. Other sulfenyl halides, such as acetylthiosulfenyl chloride and thiocyanogen chloride, have been added to alkenes, but few subsequent transformations have been carried out with those intermediates. 8... 

Thiocyanogen chloride, C1SC=N. A solution of the reagent is prepared by adding 1 mole of lead thiocyanate, Pb(SCN)2, mol. wt. 323.38 (Fisher supplies practical grade) to a solution of 2 moles of chlorine in acetic acid and filtering off the lead chloride. 

Aryl ethers and anilides, which are unreactive to thiocyanogen, react readily with thiocyanogen chloride in acetic acid to give thiocyano derivatives in high yield, ... 

A more active agent for replacement of H by SCN is thiocyanogen chloride (C1SCN), which can be prepared from lead thiocyanate and chlorine in anhydrous acetic acid.764... 

The oxidation potential of the 2 SCN = (SCN)2 couple Mis between those of the corresponding couples for Br and 1 (Table II) (38-40). The SCN = OSCN couple is comparable to the corresponding 1 couple (41). The oxidation potential of SCN relative to the halides explains the oxidation of SCN by CI2 (42) and Br2 (43) and the oxidation of 1 by (SCN)2. The latter reaction is one that can be used to quantify (SCN)2 (44). The relative oxidation potentials also facilitate the definition of inter (pseudo)halogens like I -SCN (iodine thiocyanate) (45,46) versus Cl -SCN (thiocyanogen chloride) (47) and Br -SCN (thiocyanogen bromide), which react accordingly. 

Another class of thioformimidic acid derivatives, the S-chlorides IX, is obtained by controlled addition of chlorine to isothiocyanates (io.29.30j or thiocyanogen chloride ( ). Ottmann and Hooks name... 

Chlorine reacts with sodium cyanide and sodium thiocyanate to produce cyanogen chloride and thiocyanogen chloride. The reaction of chlorine with sodium thiosulfate [7772-98-7] (Antichlor) is used to remove free chlorine from solutions. 

Cyclohexene in acetic acid added at 25° to a soln. of thiocyanogen chloride, prepared from Pb-thiocyanate and chlorine in acetic acid with subsequent addition of 2,6-di-fer -butyl-p-cresol as radical inhibitor rran -l-chloro-2-thio-cyanatocyclohexane. Y 77%. F. e. s. R. G. Guy and I. Pearson, Soc. Perkin I 1973, 281. 

Uridine or 2 -deoxyuridine give the 5-thiocyanato-derivatives by substitu-ticm with thiocyanogen chloride, " opening a route to biologically active 5-mercaptopyrimidines through dithiothreitol reduction of the thiocyanate. 

Addition of positive sulphur species, RS", usually derived from sulphenyl halides, to olefins is commonly assumed to proceed by way of thiiranium ions, the reactions often showing the stereochemistry expected for trans-addition For instance, the reaction of cyclohexene with methanesulphenyl tetrafluoroborate is believed to form an intermediate thiiranium ion (73), which then reacts with nucleophiles to give trans-methylthio-derivatives, e.g. (74). Addition of thiocyanogen chloride to olefins may... 

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