Reactions with Carbon Disulfide

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). 

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 required xanthates 1 can be prepared from alcohols 5 by reaction with carbon disulfide in the presence of sodium hydroxide and subsequent alkylation of the intermediate sodium xanthate 6. Often methyl iodide is used as the alkylating agent ... 

Chloroacetic acid, reaction with salicyl-aldehyde, 46, 28 Chloroacetone, 46, 3 Chloroacetyl fluoride, 45, 6 o-Chloroacetyl isocyanate, 46,16 -Chloroaniline, reaction with carbon disulfide and aqueous ammonia,... 

This silylene formation from 27 under mild conditions permits the synthesis of a variety of interesting carbo- and heterocycles, most of which are new types of compounds. The results are summarized in Schemes 5 and 6. The reactions with benzene and naphthalene represent the first examples of [2+1] cycloadditions of a silylene with aromatic C=C double bonds.59 623 The reactions with carbon disulfide and isocyanide (Scheme 6) are also of great interest because of their unusual reaction patterns.62b... 

The formato complex 0sH(K2-02CH)(C0)(P Pr3)2 has also been prepared by treatment of the hydride-chloro compound OsHCl(CO)(P Pr3)2 with NaOMe in benzene-methanol under carbon dioxide atmosphere. Under the same conditions, the reaction with carbon disulfide affords OsH(K2-S2COMe)(CO)(P Pr3)2.67... 

In his approach toward selenium-containing heterocycles with potential biological activity, Abdel-Hafez reacted 2-amino-3-(4,5-dihydro-17/-imidazol-2-yl)-4,5,6,7-tetrahydro-l-benzoselenophene 297 with triethyl orthoformate and benzaldehyde to generate the tricyclic systems 296 and 298, respectively (Scheme 21) <2005RJ0396>. Similarly, reaction with carbon disulfide gave the corresponding thiourea 299. 

It has been claimed (Scheme 46) <1997JIC624> that the [l,2,4]triazolopyrimidopyrimidines 169 and 170 can be prepared from a triazolopyrimidine (presumably 168) by reaction with carbon disulfide and formamide, respectively, although the paper contains a number of inconsistencies and inaccuracies, such that the final claim must be treated... 

Thiadiazinotriazolopyrimidines can be prepared in several ways from the hydrazine-substituted thiadiazino-pyrimidine 186. Reaction with carbon disulfide gives the thione 187 reaction with either anhydrides or orthoformates with sulfuric acid gives the substituted triazoles 188, and reaction with cyanogen iodide gives the aminotriazole 189 (Scheme 47) <2004HC0335>. 

As in Section 5.06.9.1, the assignments are sometimes arbitrary. Important routes to oxadiazoles, aminooxadiazoles, oxadiazolinones, and oxadiazolinethiones involving the reaction of hydrazides RCONHNH2 with carboxylic acids, acyl chlorides, alkyl esters, or trialkyl orthoesters are described in Section 5.06.9.2.1, reactions with carbon disulfide... 

The amine-terminated poly(EA) was prepared by the chain transfer polymerization of EA in the presence of the salt of aminomercaptan, followed by the reaction with carbon disulfide to give the polymeric iniferter 31. The polymerizations of St and MMA with 31 provided the triblock copolymers, poly(EA)-block-poly(St)-fcfoc/c-poly(EA) and poly(E A)-Woc/c-poly(MMA)-fcfoc/c-poly(EA), respectively, as shown in Eq. (29) [ 147] ... 

The reaction of compound 376 with hydrazine gives product 377 that has been transformed into similar triazoles 378, after reaction with carbon disulfide in the presence of alcoholic potassium hydroxide, benzoic acid in the presence of phosphoms oxychloride, or 3-[bis-(methylthiomethylene)]pentan-2,4-dione and l,l-dicyano-2,2-dimethylthioethylene, in refluxing -butanol (Scheme 40) (Table 55) <2000FES641>. 

The same starting compound 270 was also subjected to ring closure by using other reagents <2003PS1143> reaction of 270 with acetic anhydride afforded the methyl-substituted 272, whereas reaction with carbon disulfide yielded the 3-mercapto derivative 273. 

Saccharidic templates bearing an amino group in C-2, C-6, C-3, C-5. Generally, an amine located on non-anomeric position reacts similarly through the condensation reaction with carbon disulfide or thiophosgene, the preliminary formed isothiocyanate leads to spontaneous or base-induced cyclization into 1,3-oxazolidine- or l,3-oxazine-2-thiones, as previously mentioned. Several extensive studies are reported about the selective introduction of thionocarbamate moieties on carbohydrate scaffolds.3 22 23 320 34 38... 

SbCls undergoes vigorous reaction with carbon disulfide, producing carbon tetrachloride, antimony trichloride and sulfur ... 

Lead azide explodes on heating at 350°C or on percussion. Its detonation velocity is 5.1 km/sec (Meyer, E. 1989. Chemistry of Hazardous Materials, 2nshock-sensitive copper and zinc azides when mixed with the solutions of copper and zinc salts (Patnaik, P. 1999. A Comprehensive Guide to the Hazardous Properties of Chemical Substances, ed. New York John Wdey). 

Amino-5-alkyl- or 5-phenyI-l,3,4-thiadiazoles are prepared most conveniently from thiosemicarbazide. For example, benzalthiosemicarbazone by oxidation with iron(III) chloride gives the 5-phenyl derivative. Thiosemicarbazide is also used in the synthesis of 2-amino-5-mercapto-l,3,4-thiadiazole by reaction with carbon disulfide. The product may be alkylated to yield the 5-alkylthio derivatives using a variety of alkylating agents (58MI11201). 

Formamidine acetate (117) reacts with the pyrrole (118) in refluxing ethoxyethanol to give the pyrrolopyrimidine (119) which has been converted into the antibiotics toyocamycin, sangivamycin and tubercidin (Section 3.09.5) (69JA2102). A reaction with carbon disulfide... 

A one-pot synthesis of the conjugated ketenedithioacetals (7) and (8) involving indirect lithiation of propene or isobutene via the potassio deriviative reaction with carbon disulfide and 5,5-dimethylation has been reported [68]. It illustrates some aspects of the reaction of organometallics with CS2. 

The natural fibers obtained from cotton, wood, flax, hemp, and jute all are cellulose fibers and serve as raw materials for the textile and paper industries. In addition to its use as a natural fiber and in those industries that depend on wood as a construction material, cellulose is used to make cellulose acetate (for making rayon acetate yarn, photographic film, and cellulose acetate butyrate plastics), nitric acid esters (gun cotton and celluloid7), and cellulose xanthate (for making viscose rayon fibers). The process by which viscose rayon is manufactured involves converting wood pulp or cotton Iinters into cellulose xanthate by reaction with carbon disulfide and sodium hydroxide ... 

Monothiocarbamoyldiazocines 76 were converted into diazocino-dithiourazoles 77 by reaction with carbon disulfide (76JAP76-86489). Re-... 

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