Sulfolanylation of malonic acid derivatives

-Alkoxysulfolanes in the presence of equimolar amounts of sodium ethoxide react with malonic acid derivatives in which the hydrogen atom of the methylene group is activated by CN, COOR, CONH₂, and SO₂R substituents to give compounds that are identical to the products of the reaction with 2-sulfolene. A possible scheme for the reaction is proposed on the basis of the experimental data and the PMR spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 767–769, June, 1972.     

Reactions of 3-acycloxysulfolanes with nucleophilic reagents

In contrast to alkyl esters of carboxylic acids, 3-acyloxysulfolanes on reaction with nucleophilic reagents readily split out a carboxylic acid to give 2-sulfolene, which then reacts with compounds containing a labile hydrogen atom. On the basis of data on the kinetics of alkaline hydrolysis of benzoates, a scheme for elimination of the acid that includes the intermediate formation of a transition state of the E₁CB type is proposed.     

Thiirano-3,4-thiolane 1,1-dioxide and a method for its preparation

Thiirano-3,4-thiolane 1,1-dioxide was obtained by the action of triphenylphosphine sulfide on oxirano-3,4-thiolane 1,1-dioxide in the presence of an excess of trifluoroacetic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1630–1632, December, 1983.     

A study of the conditions of the formation of the cis and trans isomers of N-substituted 4-aminothiolan-3-ol 1,1-dioxides

A mixture of cis- and trans-4-alkyl(heteryl, aryl)aminothiolan-3-ol 1,1-dioxides and (3-hydroxy-1,1-dioxothiolan-4-ylamino)acetic acids have been obtained by the reaction of 2,3-dihydrothiophene-3-ol 1,1-dioxide with aliphatic, heterocyclic, and aromatic amines and aminoacetic acid. The structures of the compounds isolated has been shown by chemical and spectral methods.Translated from Khimiya Geterotskiklicheskikh Soedinenii, No. 4, pp. 475–478, April, 1980.     

Hydrolysis of carbamates and carbonates of 3-hydroxythiolane 1,1-dioxide

Alkylcarbamates of 3-hydroxy-thiolane 1,1-dioxide are hydrolyzed in the presence of bases to give alkyl(1,1-dioxo-3-thiolanyl) amines and 2-thiolene 1,1-dioxide (I). Aryl esters undergo hydrolysis to give sulfone I and 3-hydroxythiolane 1,1-dioxide (II). The corresponding alkyl- and arylcarbonates also form sulfone I and a very small amount of hydroxy derivative II under these conditions.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1482–1484, November, 1980.     

Desulfolanylation of N-sulfolanyl amino acids

N-Sulfolanyl amino acids are cleaved at the C-N bond in ammonium hydroxide and aqueous solutions of amines to give the corresponding aminosulfolanes and amino acids.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1340–1341, October, 1973.     

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 111 has given the corresponding acylated iodohydrins. The partial deactivation of the double bond of 3-sulfolenes as compared with ordinary olefins has been shown.     

Reaction of 3-AR(ALK)oxysulfolanes with amines

On the basis of data on the kinetics of the hydrolysis of 3-aroxysulfolanes in aqueous solutions of tertiary amines and in acetonitrile it is shown that the elimination of phenols is subject to specific base catalysis and occurs via an (ElcB)R carbanion mechanism. The exchange of aroxy and alkoxy groups of sulfolanyl ethers on reaction with nucleophilic reagents is explained by an elimination-addition scheme.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1188–1191, September, 1976.     

Bromocyclization of 1,1-dioxo-3-thiolen-3-yl esters of N,N-dialkyldithiocarbamic acids

Bicyclic 1,3-dithiolan-2-iminium salts were obtained by bromocyclization of 1,1-dioxo-3-thiolen-3-yl esters of N,N-dialkyldithiocarbamic acids.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1633–1634, December, 1983.