Synthesis and Dehydrobromination of 3-Bromomethyl- and 3-Bromo-3-methoxymethylcyclobutane-1-carbonitriles and Methyl 3-Bromomethyl- and 3-Bromo-3-methoxymethylcyclobutane-1-carboxylates

The anti-Markownikoff products of bromination and bromomethoxylation of 3-methylenecyclobutane-1-carbonitrile and methyl 3-methylenecyclobutane-1-carboxylate were subjected to dehydrobromination by the action of potassium tert-butoxide in THF. The reaction takes two elimination pathways: 1,3-dehydrobromination to give bicyclobutane derivatives and 1,2-dehydrobromination leading to substituted methylenecyclobutane. Structural factors in the substrate were revealed, which are responsible for the ratio of the two concurrent elimination processes.     

Synthesis of 2,5-distributed 3,3,4,4-tetracyanopyrrolidines

The reaction of 1,1,2,2-tetracyanoethane with 1-R,3-R,5-R-2,4-diazapenta-1, 4-dienes leads to 2,5-disubstituted 3,3,4,4-tetracyanopyrrolidines. The conditions for the acylation of the last were selected.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 353–358, March, 1994.     

Exciplex photonics on aerosil surface

A photochemical model reaction between anthracene and N,N-diethylaniline on aerosil has been studied. It is found that the nature of the surface is responsible for the mechanism of intermolecular interaction (dynamic or static one).     

Reaction of 3,3,4,4-tetracyanopyrrolidines with primary alcohols and amines

2,5-Substituted 3,3,4,4-tetracyanopyrrolidines react with primary alcohols in the presence of an excess of a base or with the base itself. 2-(N-Arylideneamino)-5-alkoxy-3,4-dicyanopyrroles are formed as a result of the reactions with alcohols, and 2,5-diamino-1-R-3,4-dicyanopyrroles are formed as the result of the reaction with primary aliphatic amines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1502–1507, November, 1991.     

Condensed heterocycles with a thiazole ring. 14 Nature of the electronic spectra of symmetrical polymethine dyes of the thiazolo[3,4-b][1,2,4]triazine series

Symmetrical mono-, tri-, and pentamethinecyanine dyes with a thiazolo[3,4-b][1,2,4]triazine ring were synthesized. The electron-density distributions in the dye molecules in the ground and first and second excited states were obtained by quantum-chemical calculations. It was established that the first two electron transitions are localized on the same atoms and that charge transfer to the triazine fragment of the molecule is realized in the case of excitation. The degree of participation of the heterocyclic ring in the first electron transition, which is responsible for the color of the dye, decreases with lengthening of the polymethine chain.See [1] for communication 13.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 24, No. 3, pp. 418–423, March, 1988.     

Structure and reactivity of 3- and 4-[(4′-chlorophenyl)sulfamoyl]-1-diazoalkan-2-ones

Conclusions Under the conditions of the acidic cyclization reaction of homologous 3- and 4-[(4-chlorophenyl)sulfamoyl]-1-diazoalkan-2-ones, the formation of the five-membered heterocycle, a pyrrolidin-3-one derivative, is more convenient than the formation of the four-membered heterocycle- an azetidin-3-one derivative. These results are in agreement with the differences in conformations of diazoalkane molecules in the crystalline state.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 134–138, January, 1986.     

Intramolecular reactions in acyclic phosphaalkenes

Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 24, No. 6, pp. 685–695, November–December, 1988.     

Chemistry of 1,1,2,2-tetracyanoethane. 11. Synthesis and stereochemical characteristics of 3-methyl-5-oxo-2′-amino-5′-phenyl -3′,4′,4′-tricyanoisoxazoline-4-spiro-1′-cyclopent-2′-ene

The Michael condensation of 1,1,2,2-tetracyanoethane with 3-methyl-4-benzylideneisoxazolin-5-one having the Z configuration leads to a heterocyclic spiran with retention of the cis orientation of the phenyl and keto groups. The deviations of the series of bond angles of the spiran from the standard values, the abnormal lengths of the C-C bonds adjacent to the gem-dicyano group, and the appearance of nonbonding >C=O(...)CN interactions and conjugation effects in the enaminonitrile fragment are discussed.For Communication 10, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1404–1410, October, 1988.