Investigation of substituted 2- and 3-thiolene 1,1-dioxides by PMR spectroscopy with the aid of a lanthanide shift reagent

The reaction of lanthanide shift reagent Eu(FOD)₃ with 3-phenyl- and 3- and 4-chloro-2-thiolene 1,1-dioxides and with 3-phenyl-3-thiolene 1,1-dioxide was investigated by PMR spectroscopy. The geometrical structure of the adduct of the lanthanide shift reagent with 4-chloro-2-thiolene 1,1-dioxide was found.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 314–317, March, 1984.     

Condensed thiolane 1,1-dioxide systems. 3. Two modes of cyclization of N-substituted trans-3-chloro-4-thioureidothiolane 1,1-dioxides

Reaction of trans-3-chloro-A-aminothiolane 1,1-dioxide hydrochloride with aryl isothiocyanates gives, according to the base involved, cis-perhydrothieno[3,4-d]imidazole-2-thione 5,5-dioxides or the hitherto undescribed cis-2-aryliminoperhydrothieno 3,4-d] thiazole 5,5-dioxides.For Part 2, see [1].Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1420–1423, October, 1988.     

Isomerization of 3-aryl-4-sulfolenes and their reaction with some nucleophilic reagents

Bases convert 3-(4-substituted phenyl)-4-sulfolenes to 3-aryl-3-sulfolenes, which are subsequently isomerized to 3-aryl-2-sulfolenes. The ratios of the products depend on the character of the substituent in the phenyl ring, and electron-acceptor substituents accelerate the isomerization.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1072–1077, August, 1975.     

Reaction of sulfolanyl sulfonates with some nucleophilic reagents

The corresponding -substituted sulfolane derivatives were isolated in the reaction of 3-sulfolanyl arene(alkane)sulfonates with amines, alcohols, and mercaptans. Depending on the nature of the nucleophile, 3,4-disubstituted sulfolanes and 4- and 3-substituted 2-sulfolenes were obtained with 3,4-sulfolanyl disulfonates and 4-sulfolen-2-yl sulfonates.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 625–630, May, 1974.     

Reaction of dithiocarbamic acid salts with 4-substituted 2-thiolene- and 3,4-disubstituted thiolane 1,1-dioxides. Structural studies of N-phenylthiolano[3,4-d]thiazolidine-2-thione 5,5-dioxide

The reaction of monoalkyl(aryl)dithiocarbamic acid salts with 4-substituted 2-thiolene and 3,4-disubstituted thiolane 1,1-dioxides gave N-alkyl(aryl)thiolano-[3,4-d]thiazolidine-2-thione 5,5-dioxides, the structure of which was proved by x-ray diffraction studies. 1,1-Dioxothiol-3-en-3-yl esters were obtained with salts of dialkyl(heteryl)dithiocarbamic acids.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 907–912, July, 1981.     

Spectral investigation of intramolecular interaction in sulfur-organic compounds

Earlier¹ it was reported that 4-aryl-4,5-dihydrothiophene-1,1-dioxides (I) are converted in aqueous and alcohol solution of bases to isomeric 3-aryl-2,5-dihydrothiophene dioxides (II) and 3-aryl-4,5-dihydrothiophene-1,1-dioxides (III) (Fig. 1).In the presence of electron-donor substituents in the p-position of the phenyl ring, IIb, c compounds are practically irreversibly isomerised to III b, c. For unsubstituted phenyldihydrothiophene-1,1-dioxides IIa and IIIa the reaction proceeds riversibly but equilibrium is shifted towards isomer IIIa indicating its high thermodynamic stability. It is known² that 2,5-dihydrothiophene-1,1 -dioxide is more stable than 4,5-dihydrothiophene-1,1-dioxide. Consequently, the observed stability increase of 3-aryl-4,5-dihydrothiophene-1,1-dioxides (IIIa–c) is due to interaction of the substituent C₆H₄X with the sulfonyl group. This paper investigates the nature of this interaction.     

Sulfur-containing derivatives of five-membered cyclic sulfones. 1. Synthesis of salts of isothioureidothiolene 1,1-dioxides

Salts of isothioureidothiolene 1,1-dioxides with different positions of the ring double bond were obtained by the reaction of thiourea with halo derivatives of thiolene 1,1-dioxides.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 36–39, January, 1988.     

Synthesis and some properties of amides of 4-carboxymethyl-2-thiolene 1,1-dioxide

Amides of 4-carboxymethyl-2-thiolene 1,1-dioxide were obtained with aliphatic, heterocyclic, and aromatic amines. A study was carried out on the reactions of these amides with various nucleophilic reagents.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1622–1625, December, 1984.     

Reaction of 4-arylamino-2-sulfolenes with nucleophilic reagents

The nucleophilic reactions of 4-arylamino-2-sulfolenes with amines, alcohols, and mercaptans give 3-arylamino-2-sulfolenes and 3,4-substituted arylaminosulfolanes, the ratio between which depends on the nature of the reagents and the conditions.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1332–1334, October, 1974.     

Reaction of sulfolenes with silver salts of carboxylic acids and halogens

The reaction of sulfolenes with silver salts of carboxylic acids and iodine at a ratio of 1∶1∶1 has given the corresponding acylated iodohydrins. The partial deactivation of the double bond of 3-sulfolenes as compared with ordinary olefins has been shown.