Mercury dithiol complexes

Complex formation between metals and l,2-dithiole-3-thiones has long been known. The mercury(II) complex is often used for purification of 1,2-dithiole-3-thiones.1... 

P-Azo-[2-methyl-1,2-dicarbadecaborane( 14)], 2624 2-Azoxyanisole, 3653 1,4-Benzenediol-oxygen complex, 2334 Benzeneperoxy sulfonic acid, 2341 Benzeneseleninic acid, 2335 Benzeneseleninic anhydride, 3495 Benzenethiol, 2344 2,2 -Bi-l,3-dithiole, 2215 2,2 -Bipyridyl 1-oxide, 3258 Bis(cyclopentadienyl)lead, 3294 Bis-A(imidosulfurdiiluoridato)mercury, 4342 Bismuth trisulfide, 0234... 

N-(2,3-Dimercaptopropyl)phthalamidic acid (41, DMPA) has been shown to form relatively stable complexes with cadmium, zinc and mercury312. DMPA has also been shown to enhance faecal and urinary excretion of mercury in mice and arsenic in mice and rabbits. For the decorporation of arsenic, taken in as arsine, the administration of 3-(tolylthio)propane-l, 2-dithiol (42) has been proposed in the USSR313. ... 

Sodium hydrosulfide regenerates l,2-dithiole-3-thiones from their mercury(II) chloride complexes. This may be regarded as a nucleophilic attack <66AHC(7)39). 

Conversion of the l,2-dithiole-3-thiones 267 into corresponding 5-alkyl- or 5-arylthio-37/-l,2-dithiol-3-ones in low to moderate yields (18-70%) was acomplished with mercury acetate in glacial acetic acid <2007ARK279>. The yields are not high due to the complexity of the remaining residue. 

British Anti-Lewisite (BAL) is a dithiol used as an antidote in mercury poisoning. It was originally developed as an antidote to a mustard-gas-hke chemical warfare agent called Lewisite. Lewisite was developed near the end of World War I and never used. By the onset of World War II, Lewisite was considered to be obsolete because of the discovery of BAL, an effective, inexpensive antidote. The two thiol groups of BAL form a water-soluble complex with mercury (or with the arsenic in Lewisite) that is excreted from the body in the urine. 

C=0. It is therefore susceptible to nucleophilic attack at carbon. Methods have been developed by which this polarization is effectively reversed so that the carbon atom itself becomes the nucleophilic centre. Such an inversion is known as umpolung. An example is provided by the 1,3-dithiane system. An aldehyde may be converted into a cyclic dithioacetal by reaction with propane-1,3-dithiol in the presence of an acid. The two adjacent electronegative sulphur atoms make the C—H bond of this acetal rather acidic. Treatment with butyllithium therefore affords a lithio derivative in which the carbon atom is susceptible to electrophilic attack. The 1,3-dithiane system is reconverted into a carbonyl group by acid hydrolysis in the presence of mercury(II) ions, which complex with the dithiol. The RCO group in the original aldehyde is thus equivalent to R—C=0 (Fig. 3.10). 

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