Sodium alkylmercaptides

From a study of the action of sodium alkylmercaptides on methyl 2,3-anhydrohexosides, Reichstein and his colleagues were able to develop a new method for the preparation of desoxysugars. When methyl 2,3-anhydro-4,6-benzylidene-a-D-alloside (XL) was heated under reflux with sodium methylmercaptide in methanol solution, cleavage of the anhydro ring occurred, and after purification by chromatographic procedures, methyl 4,6-benzylidene-2-methylthio-2-desoxy-a-D-altroside (XLI) was obtained. Hydrogenation of this in the presence of Raney nickel readily converted it into methyl 2-desoxy-a-D-alloside (XLII).162,163... 

Nitro groups, which are readily introduced into the imidazole ring,269,388 445 can be reduced chemically or catalytically to amino groups.227,446 Nitro substituents facilitate the displacement of adjacent halogen substituents,447 e.g., the chloro group of 5-chloro-4-nitroimidazole can be replaced by an alkylmercapto group using sodium alkylmercaptide and sodium ethoxide in ethanol. 

With pyridine 1-oxide, sodium phenylmercaptide gives only pyridine, but with l-alkoxy-2- and -4-picolinium salts, reaction occurs at the methyl groups producing phenyl-2- and -4-pyridylmethylsulphide, respectively. However, l-alkoxy-4-picolinium salts react with alkylmercaptides both laterally and at the nucleus, giving by the latter mode both 2- and 3-alkylmercapto-4-methylpyridine. The 2-isomer presumably arises by direct nucleophilic substitution, and the 3-isomer may be formed ... 

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See also in sourсe #XX -- [ ]

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