Phenyl thiocyanate

Methyl acetate Phenyl thiocyanate Propyl benzoate... 

Methyl Acetate Phenyl Thiocyanate Propyl Benzoate... 

PHENYLTHIOCARBAMIDE see PGN250 PHENYL THIOCYANATE see TFF600 PHENYLTHIONOPHOSPHONIC DICHLORIDE see PFW200... 

Reaction of sodium thiocyanate with triphenylbismuth dichloride (3) leads directly to phenyl thiocyanate. Although no intermediate was detected, the reaction is likely to proceed by ligand coupling of a pentavalent thiocyanate derivative. ... 

Thiocyanogen Diphenylthiocyanobismuthme, bismuth thiocyanate, polymerised thiocyanogen and phenyl thiocyanate Challenger and Wilkmson, Trans. Ghem Soc., 1922, 121, 91. 

RCOSCeHg, are formed from acids and phenyl thiocyanate. In this reaction only 1.1 equiv. of the triallcylphosphine is necessary for satisfactory yields (80-95%). 

This reaction was first reported by Riemschneider in 1949. It is an acidic transformation of alkyl or aryl thiocyanates into thiocarbamates and is known as the Riemschneider reaction. In this reaction, when thiocyanates are treated with concentrated sulfuric acid, the corresponding thiocarbamates are obtained. In parallel, when thiocyanates are treated with concentrated sulfuric acid in the presence of alcohol or olefin, the corresponding A -substituted carbamates are yielded. The alcohols or olefins that are stable in the presence of sulfuric acid, including isopropyl alcohol, cc-butyl alcohol, r-butyl alcohol, cyclohex-anol, isobutylene, and camphene aU are suitable for this reaction, whereas low-order alcohols such as methanol and ethanol do not react with thiocyanate to give the corresponding A -substituted thiocarbamates. hi addition, the benzyl thiocyante and some ortho-substituted phenyl thiocyanates cannot be transformed into the corresponding thiocarbamates under these conditions because they are sensitive to sulfuric acid. Some unsuitable thiocyanates are o-carboxyl, o-methoxy, o-nitrophenyl thiocyanates, and o-methyM-amino phenyl thiocyanate. ... 

Illustrated below is the mechanism for the reaction between phenyl thiocyanate and a general alcohol. 

A benzene solution of 2 g phenyl thiocyanate was treated slowly under shaking and ice cooling with 10 mL 95% H2SO4. The mixture was kept at 0-5°C for 15 h and then poured on ice. The precipitate was collected, washed with water, and dried in air. The phenylthiocarbamate was a needle crystal, m.p. 98°C the yield was 87%. 

To a mixture of concentrated sulfuric acid and 1.85 g -butyl alcohol (25 mmol), was added 3.4 g phenyl thiocyanate (25 mmol) dropwise under stirring. After all the phenyl thiocyanate was added to the solution, the stirring was continued for 5 h with cooling on an ice bath. Then the reaction mixture was stirred into 250 mL ice water to yield yellow crystals, which were further purified by recrystallization several times from hexane following treatment with activated charcoal, m.p. 115°C. The yield was 40%. 

To a mixture of 30 mL glacial acetic acid and 5 mL 95% sulfuric acid, was added 7.0 g phenyl thiocyanate (51 mmol) dropwise. At the same time, a slow stream of isobutylene was passed through the reaction mixture at a temperature of 10°C within 40 min, the reaction mixture absorbed 6.0 g isobutylene (107 mmol). After being maintained at 10°C for 24 h, the contents of the reaction vessel were poured into 250 mL ice water, and extracted with ether. The combined ethereal solution was dried and evaporated. The residue was fractionated to give 5.5 g phenyl thiocyanate (71-73°C at 1.5 mmHg), the residue remained after the distillation was recrystallized from hexane to afford 0.7 g A-Lbutyl phenylcarbamate, in a yield of 30.1% based on 21.4% conversion. 

A standard condition has been optimized for this reaction, in which the aryl amine is diazotized in 10 times its amount of acetic acid, followed by the addition of one equivalent of cuprous halide in hydrohalic acid. Under these conditions, the acetate salt of aryl amine is relatively soluble, and less froth and tarry material are formed during diazo transformation. In addition, chlorination, bromination, and iodonation of p-haloaniline to dihalobenzenes under such standard conditions give almost comparable average yields. Other modifications of this reaction include the formation of phenyl selenocyanate by the reaction with potassium selenocyanate, and aryl nitrile by the reaction with nickel cyanide. Moreover, this reaction has been extended to the preparation of phenyl thiocyanate, phenyl isothiocyanate and aromatic sulfonyl chloride. ... 

Ar. thiocyanates. A soln. of N-(phenylthio)isatin in chloroform stirred vigorously 1 hr. at room temp, with excess aq. NaCN-soln. phenyl thiocyanate. Y 90%. F. e., also prepn. of thioethers and disulfides, s. M, Furukawa, T. Suda, and S. Hayashi, Chem. Lett. 1974, 881. 

Ph3P)3Pd has been reported to catalyse the highly regioselective addition of phenyl thiocyanate to terminal alkynes. ... 

Molecular ion Dominant base peak in phenyl thiocyanate. Odd mass for odd number of N atoms in the molecule. Characteristic isotope peak at [M+2] " and [Frag+2] for S-containing fragments (per S atom 4.4% relative to M" "). 

C14H12N2O3S2 4-amino-3-hydroxy-phenyl-thiocyanic acid ester, p-toluene sulfonate... 

C15H14N2O2S1 4-amino-3-(2-phenoxy ethoxy)phenyl thiocyanic acid ester... 

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