<b>Thiacyanocarbons. II. Chemistry of Disodium Dimercaptomaleonitrile</b>

Simmons, Howard E.; Blomstrom, Dale C.; Vest, Robert D.

doi:10.1021/ja00883a029

Cited by 108 publications

(23 citation statements)

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“…To a stirred chloroform solution (50 mL) of 4-(benzoylthio)-5-(methylthio)-2-thioxo-1,3-dithiole [27] (10 mmol, 3.16 g) (for 1a) or 1-(benzoylthio)-1,2-dicyano-2-(methylthio)ethene [28] (2.60 g) (for 1b) was added cesium hydroxide hydrate (10 mmol, 1.70 g) in methanol (10 mL). After about 1 min, the cesium thiolates started to separate.…”

Section: Cesium 4-(methylthio)-2-thioxo-13-dithiole-5-thiolate (1a) mentioning

confidence: 99%

Syntheses and Crystal Structures of Coinage Metal Thioether-Thiolato Complexes

Zeltner

Jelonek

Sieler

et al. 2001

Eur. J. Inorg. Chem.

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Keywords: Sulfur ligands / Copper / Silver / GoldCopper(I), silver(I), and two gold(I) complexes of the type (Ph 3 P) n M(L) [n = 1, 2, 3; L = 4-(methylthio)-2-thioxo-1,3-dithiole-5-thiolate (L a ), 1,2-dicyano-1-(methylthio)ethene-2-thiolate (L b )] have been synthesized. The molecular structure of these complexes was determined by X-ray crystallography and shows differences in the coordinated sulfur atoms as well as in the coordination geometry of these (Ph 3 P) n M(L) com-

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Section: Cesium 4-(methylthio)-2-thioxo-13-dithiole-5-thiolate (1a) mentioning

confidence: 99%

Syntheses and Crystal Structures of Coinage Metal Thioether-Thiolato Complexes

Zeltner

Jelonek

Sieler

et al. 2001

Eur. J. Inorg. Chem.

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“…Methyl Cyanodithioformate (1) This compound was prepared according to Simmons et al (13). The residual syrupy mixture, 2ab, gave the n.m.r.…”

Section: General Conditionsmentioning

confidence: 99%

“…This has been demonstrated in our laboratory by the formation of Diels-Alder adducts with a wide range of dienes differing in reactivity from that of cyclopentadiene to that of 1,3-butadiene. The reagent is easily synthesized (12,13) and is deep purple in color, a property which is useful to indicate the completion of the reaction, or to signal the occurrence of a retroDiels-Alder reaction during the workup of the adducts. Such a dienophile has the advantage over the fluorothiocarbonyl compounds and others of introducing a potentially more useful functional group (cyano) into the product.…”

Section: Introductionmentioning

confidence: 99%

Methyl Cyanodithioformate as a Reactive Dienophile in Diels–Alder Reactions

Vyas¹,

Hay²

1971

Can. J. Chem.

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A Diels-Alder reaction between cyclopentadiene and methyl cyanodithioformate afforded ,a 60:40 mixture of the isomers 2a and b. The n.m.r. studies of these compounds and the products of LiAlH4 reduction, 3a and b, established that the major isomer, 2a, was 3-exo-cyano-3-methylthio-2-thiabicyclo-[2.2.l]hept-Sene, and that 3a was the corresponding 3-exo-aminomethyl compound.Une rCaction de Diels-Alder entre le cyclopentadiene et le cyanodithioformate de methyle conduit a un mClange 60:40 des isomeres 2a et b. Une Ctude r.m.n. de ces composes et des produits de reduction par LiAlH,, 3a et b, prouve que le produit majoritaire, 2a, est le cyano-3 exo mtthylthio-3 thia-2 bicyclo[2.2.l]heptene-5; le produit 3a est l'aminoethyl-3 exo correspondant.

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“…Treatment of compound 1b with compound 2b (R 1 = Me, R 2 = Et, R 3 = H) (2.6 equivalents) in dimethyl sulfoxide (10 ml) for 4 days at room temperature gave 3-amino-2-[2-(2-amino-1-ethoxycarbonylpropenylsulfanyl)-1,2-dicyanovinylsulfanyl]-2-butenoic ethyl ester 4b (x = 1, R 1 = Me, R 2 = Et, R 3 = H) (18%) together with 1,4-thiazine derivative 5 (10%), tetrasulfide 6 (13%), a minute amount of sulfur, and unknown mixtures, which were inseparable by chromatography and high performance liquid chromatography [(µBodapak C18,10 µm,7.8 x 300 mm ID), differential refractometer, acetonitrile]. Of the isolated compounds, compound 5 was obtained by treatment of compound 1a with compound 2b under the same conditions [1].…”

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confidence: 99%