Heterocyclic compounds sulfur

Sulfur containing heterocycles are also common Compounds m which sulfur is the heteroatom m three four five and six membered rings as well as larger rings are all well known Two interesting heterocyclic compounds that contain sulfur-sulfur bonds are hpoic acid and lenthiomne... 

Substances that contain one or more atoms other than carbon as part of a nng are called heterocyclic compounds Rings m which the heteroatom IS oxygen nitrogen or sulfur rank as both the most common and the most important... 

Sulfonium Compounds. Sulfonium compounds of the type R R R S X are named by citing in alphabetical order the radical names followed by -sulfonium and the name of the anion. For heterocyclic compounds, -ium is added to the name of the ring system. Replacement of > CH by sulfonium sulfur is denoted by the prefix thionia-, and the name of the anion is added at the end. 

Huisgen has reported in 1963 about a systematic treatment of the 1,3-dipolar cycloaddition reaction as a general principle for the construction of five-membered heterocycles. This reaction is the addition of a 1,3-dipolar species 1 to a multiple bond, e. g. a double bond 2 the resulting product is a heterocyclic compound 3. The 1,3-dipolar species can consist of carbon, nitrogen and oxygen atoms (seldom sulfur) in various combinations, and has four non-dienic r-electrons. The 1,3-dipolar cycloaddition is thus An +2n cycloaddition reaction, as is the Diels-Alder reaction. 

Unlike carbocyclic (or homocyclic) hydrocarbons which have been discussed previously, heterocyclic compounds contain in their rings other atoms, such as nitrogen, oxygen, or sulfur, in addition to carbon. Some examples are shown below ... 

Silylthioaldehydes 103, reactive dienophiles formed in situ from acetals according to a general method, are directly trapped with dienes to afford sulfur-containing heterocyclic compounds in good yield (Equation 2.29). Silylthioaldehydes are quite reactive in comparison with the aliphatic ones [102] which are rather inert in the cycloaddition reactions. 

The latter reagent also methylates certain heterocyclic compounds (e.g., quinoline) and certain fused aromatic compounds (e.g., anthracene, phenanthrene). The reactions with the sulfur carbanions are especially useful, since none of these substrates can be methylated by the Friedel-Crafts procedure (11-12). It has been reported that aromatic nitro compounds can also be alkylated, not only with methyl but with other alkyl and substituted alkyl groups as well, in ortho and para positions, by treatment with an alkyllithium compound (or, with lower yields, a Grignard reagent), followed by an oxidizing agent such as Bra or DDQ (P- 1511). 

The reaction between ketones, sulfur, and ammonia can also lead to heterocyclic compounds. For a review, see Asinger, F. Offermanns, H. Angew. Chem. Int. Ed. Engl., 1967, 6, 907. 

Kuhn EP, JM Suflita (1989) Microbial degradation of nitrogen, oxygen and sulfur heterocyclic compounds under anaerobic conditions studies with aquifer samples. Environ Toxicol Chem 8 1149-1158. 

In this article, a description has been given of recent investigations in the field of thiepin chemistry which are important for the major seven-membered unsaturated heterocyclic compounds. While the properties of these sulfur heterocycles have been determined quite well, some important questions still remain unexplored. Our current research efforts involve attempts to understand more generally the substituent effects on the thermal stability of the thiepin. 

Girgis, M. J., and Gates, B. C., Catalytic Hydroprocessing of Simulated Heavy Coal Liquids. 2. Reaction Networks of Aromatic Hydrocarbons and Sulfur and Oxygen Heterocyclic Compounds. Ind. Eng. Chem. Res, 1994. 33 pp. 2301-2313. 

PEC. The patent includes the production method for the biocatalyst, with a characteristic inhibitory effect on certain enzyme expression. The expression recombinant vector contains a promoter free from manifesting inhibition due to an inorganic sulfur compound or a sulfur-containing amino acid. The recombinant microorganism also contains a gene for desulfurizing the sulfur-containing heterocyclic compound. 

The research was oriented towards the development of biocatalysts for removal of recalcitrant sulfur heterocyclic compounds including benzothiophenes, naphthothio-phenes, and alkylbenzothiophenes. To begin with, they focused on asymmetric sulfur compounds in this class and developed a method for desulfurization of these compounds present in petroleum products [108], The identity of the microorganisms was not disclosed in the abstract but they do claim use of the enzymes as well in the application. 

Two patents were awarded on microbial desulfurization of sulfur-containing heterocyclic compound [155,156], the first targeting DBT and alkylated DBTs and the other benzothiophenes and alkylated benzothiophenes. In both cases, the selective cleavage of the C—S bonds is reported as the main mechanism. The claimed bacteria strains are Mycobacterium G3 strain (PERM P-16105) and R. erythropolis KA2-5-1 strain (PERM P-16277), respectively. Special emphasis was made to the desulfurization of the recalcitrant 4,6-dimethyl-dibenzothiophene. The main product from DBT... 

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