Dithiole-2-thione

A range of 4-substituted l,3-dithiole-2-thiones (71) and 2,6-substituted 1,4-dithiafulvalenes (73) were synthesised from 4-substimted 1,2,3-thiadiazoles (72). Reaction of (72) with NaH in a mixture of CS2 and acetonitrile led to the formation of (71), whereas absence of CS2 gave fulvalenes (73). This route was found to be very efficient for the preparation of 4-formyl-1,3-dithiole-2-thione (71 R = CHO), which was previously difficult to prepare, and thus allowed the synthesis of the novel 2,6(7)-bisformyltetraAiafulvalene (74) <96T3171>. 

Attempts to follow a published procedure for the preparation of 1,3 -dithiole-2-thione-4,5-dithiolate salts [1], involving reductive coupling of carbon disulfide with alkali metals, have led to violent explosions with potassium metal, but not with sodium [2], However, mixtures of carbon disulfide with potassium-sodium alloy, potassium, sodium, or lithium are capable of detonation by shock, though not by heating. The explosive power decreases in the order given above, and the first mixture is more shock-sensitive than mercury fulminate [3],... 

Bismorpholino disulfide (35) and related compounds are prepared from the corresponding amine (or imide) and disulfur dichloride. An elegant synthesis of the 1,3-dithiole-2-thione (36) from 35 is shown this is an example of two transfer reagents acting in concert.40... 

Ethylenediaminetetraacetic acid, analogs, complexes of, 3 277 chelation by, 3 276-277 cobalt complex of, 3 281 complexes, 3 277-278 formation constant of, 3 273-274 -nickel, 3 17-18 stability of, 3 266-267 reaction with metal ions, 3 62 Ethylene dibromide, irradiation of, 5 196 4,5-Ethylenedithio-1,3-dithiole-2-thione based supramolecular complexes, 46 200-204 Ethylene glycol, 32 4... 

In the past, TTF has been prepared from 1,3-dithiole-2-thione, which, by an oxidative step, was converted to a 1,3-dithiolylium salt followed by coupling with base.6 9,15 The present method uses a reductive sequence, thereby permitting milder conditions and better yields.16... 

The most frequently used designation dmit (dimercaptoisotrithione) for the ligand (83) may not be the best choice (the name ethylenetrithiocarbonatedithiolate or trithionedithiolate would seem more appropriate and 1,3-dithiol-2-thione-4,5-dithiolate would seem accurate), but it has established itself throughout this corner of the chemical literature. 

Dithiole-2-thione-4,5-dithiolate salts, 112 Drums (barrels), 112... 

Recently, it has been reported that 1.3-dithiole-2-thione (12) reacts with primary amine to give the corresponding thiourea and A-4-thiazoline-2-thione (Scheme 5) (14). 5-Methylenethiazolidine-2-thione (131 obtained from the reaction of propargyl amine and carbon disulfide... 

Upon treatment with CS2 at 170°C, 4,6-dihydro thieno[3,4-d]-l,2,3-thiadiazole (70) yielded 4,6-dihydrothieno[3,4-(/]-1,3-dithiole-2-thione (71), which was a useful intermediate for the synthesis of a novel organic conductor <89TL7249>. 

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