With carbon disulfide

Reactions were carried out by condensing a-aminonitriles [NCCHiRiiNHJ with carbon disulfide in the presence of aldehydes (R CHO) or ketones [Pg.287]

Methyiaminoacetonitrile (216) reacts with carbon disulfide in the presence of acetic anhydride with ethyl acetate as solvent to give 2-thio-3-methyl-A-4-thiazoline in 74% yield (Scheme 113a) (326). If the reaction is carried out using benzaldehyde in place of acetic anhydride, the corresponding 5-benzylideneamino derivative of 217 is obtained in 70% yield. 

Another example of condensation with carbon disulfide is shown in (Scheme 113b) (774). 

Ethylisocyanoacetate with carbon disulfide leads to the 1,3-thiazole in 49% yield (Scheme 147) (778). 

Rayon. Viscose rayon is obtained by reacting the hydroxy groups of cellulose with carbon disulfide in the presence of alkali to give xanthates. When this solution is poured (spun) into an acid medium, the reaction is reversed and the cellulose is regenerated (coagulated). 

Synthesis from Thiohydantoins. A modification (71) of the Bucherer-Bergs reaction consisting of treatment of an aldehyde or ketone with carbon disulfide, ammonium chloride, and sodium cyanide affords 2,4-dithiohydantoias (19). 4-Thiohydantoias (20) are available from reaction of amino nitriles with carbon disulfide (72). Compounds (19) and (20) can be transformed iato hydantoias. 

The various fumigants often exhibit considerable specificity toward insect pests, as shown in Table 8. The proper choice for any control operation is determined not only by the effectiveness of the gas but by cost safety to humans, animals, and plants flammabdity penetratabdity effect on seed germination and reactivity with furnishings. The fumigants may be used individually or in combination. Carbon tetrachloride has been incorporated with carbon disulfide, ethylene dichloride, or ethylene dibromide to decrease flammability, and carbon dioxide is used with ethylene oxide for the same purpose. 

Electronic excitation from atom-transfer reactions appears to be relatively uncommon, with most such reactions producing chemiluminescence from vibrationaHy excited ground states (188—191). Examples include reactions of oxygen atoms with carbon disulfide (190), acetylene (191), or methylene (190), all of which produce emission from vibrationaHy excited carbon monoxide. When such reactions are carried out at very low pressure (13 mPa (lO " torr)), energy transfer is diminished, as with molecular beam experiments, so that the distribution of vibrational and rotational energies in the products can be discerned (189). Laser emission at 5 p.m has been obtained from the reaction of methylene and oxygen initiated by flash photolysis of a mixture of SO2, 2 2 6 (1 )-... 

Diarylamines do not react with carbon disulfide, whereas dialkylamines readily form dithiocarbamates. However, N,Ar-diaryldithiocarbamates can be prepared from metal salts of diarylamines and carbon disulfide (15). They are more stable than diaLkyldithiocarbarnic acids, eg, N,N -diphenyldithiocarbamic acid [7283-79-6] mp 142°C. Similarly, various metal salts of DPA react with carbon dioxide and an epoxide to give the P-hydroxyalkyldiphenylcarbamates (16). 

Agricultural grades of ammonium thiosulfate are prepared by similar processes and contain some excess sulfur. The sulfur can be removed by washiug with carbon disulfide. A typical sulfur-free product contaius 87% (NH 2S203 3.4% (NH 2SC)3, and 9.6% (NH 2SC)4 (67). 

The alkah metal xanthates are generally prepared from the reaction of sodium or potassium hydroxide with an alcohol and carbon disulfide. The initial reaction is the formation of the alkoxide, which reacts with carbon disulfide to give the xanthate ... 

Powdered KOH ia DMF (dimethylformamide) or DMSO reacts with carbon disulfide to give these xanthates. 

Several cellulose esters (qv) are prepared commercially. Cellulose xanthate [9032-37-5] is made by reaction of cellulose swollen in 8.5—12% sodium hydroxide solution (alkaU cellulose [9081-58-7J) with carbon disulfide and is soluble in the alkaline solution in which it is made. When such a solution, termed viscose, is introduced into an acid bath, the cellulose xanthate decomposes to regenerate cellulose as rayon fibers or cellophane sheets (see Fibers, REGENERATED CELLULOSICS). 

Ethylenediamine reacts with carbon disulfide ia alcohoHc solution to give ethylenethiourea (2-imida2oHdinethione [96-45-7]). 

Potential Processes. Sulfur vapor reacts with other hydrocarbon gases, such as acetjiene [74-86-2] (94) or ethylene [74-85-1] (95), to form carbon disulfide. Higher hydrocarbons can produce mercaptan, sulfide, and thiophene intermediates along with carbon disulfide, and the quantity of intermediates increases if insufficient sulfur is added (96). Light gas oil was reported to be successflil on a semiworks scale (97). In the reaction with hydrocarbons or carbon, pyrites can be the sulfur source. With methane and iron pyrite the reaction products are carbon disulfide, hydrogen sulfide, and iron or iron sulfide. Pyrite can be reduced with carbon monoxide to produce carbon disulfide. 

The EBDCs are prepared by reaction of EDA with carbon disulfide in the presence of sodium or ammonium hydroxide initially, then with 2inc and/or manganese salts, as appropriate (156—160). A continuous process has recendy been reported (161). The common names of these salts are nabam [142-59-6] (Na salt), amobam (ammonium salt), 2ineb [12122-67-7] (Zn salt), maneb [12427-38-2] (Mn salt), andmanco2eb. 

Experiments with cyclic thioethers (80JCS(P1)1693), thiourea, thiocyanate and ethyl xan-thate always led to destruction of oxaziridines (73AJC2159). Products of complicated consecutive reactions could be isolated but only with some difficulty, e.g. (92) from a reaction with carbon disulfide (74JOC957), and (93), obtained by trapping with butadiene a product of a reaction between an oxaziridine and a thiirane (80JOC1691). 

Azirine, trans-2-methyl-3-phenyl-racemization, 7, 33, 34 1-Azirine, 2-phenyl-reactions, 7, 69 with carbon disulfide, S, 153 1-Azirine, 3-vinyl-rearrangements, 7, 67 Azirines, 7, 47-93 cycloaddition reactions, 7, 26 fused ring derivatives, 7, 47-93 imidazole synthesis from, 5, 487-488 photochemical addition reactions to carbonyl compounds, 7, 56 photolysis, 5, 780, 7, 28 protonated... 

Methanol with carbon disulfide, cyclohexane or petroleum ether. 

Thiohydantoin 9 was obtained from the treatment of carbonyl 1 with carbon disulfide and ammonium cyanide in aqueous methanol. The transformation could also be carried out step-wise, that is, treatment of 1 with ammonium cyanide to form aminonitrile 10 followed by reaction with carbon disulfide to produce thiohydantoin 9. Alternatively, 5,5-disubstituted 4-thiohydantoins could be prepared by the reaction of ketones with ammonium monothiocarbamate and sodium cyanide. ... 

The same diamine, when treated with carbon disulfide in alkaline medium, yielded 2-mercapto- l//-imidazo[4,5-/]quinoline (88PS267,88SC973,86IJC264), which, on treatment with alkyl, aralkyl, and acid halides, gave the corresponding thioethers and thioesters 111, respectively (88PS267, 86IJC264). 

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