Chlorination of aromatic substrates catalyzed by the phthalocyanine complexes

The chlorination of benzene, toluene, and o-xylene with molecular chlorine in the presence of the phthalocyanine complexes of different structures was studied. The transformations of the catalysts during the reaction were investigated. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1644–1647, August, 2008.     

Synthesis and Structure of Mixed Phosphonium-iodonium Ylide

A mixed phosphonium-iodonium ylide, phenyliodoniumethoxycarbonylmethylenetriphenylphosphorane borofluoride, was synthesized. Its structure was established by means of X-ray diffraction analysis. Temperature dependence of ¹H, ¹³C, and ³¹P spectra of the ylide synthesized was investigated. A dynamic equilibrium between Z and E-isomers was observed.     

Arene sulfenylation by arenesulfenamides and arenesulfenylacetates

Two systems for arene sulfenylation were investigated: arenesulfenamides in the presence of SO₃ and sulfenylacetate complexes with AlBr₃. A preference for the second reagent was demonstrated for sulfenylation of substrates bearing donor substituitents.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 324–326, February, 1995.     

Regiochemistry of the addition of mercury salts to bornylene

The dependence of the regiochemistry of the mercuration of bornylene on the nature of the mercurating reagent and on the solvent has been found. The structures of the intermediate and transition state in these reactions have been proposed.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 501–505, March, 1994.     

Nucleophilic Opening of the Aziridine Ring in 1-Alkyl-1-azoniatricyclo[2.2.1.02,6]heptanes

Opening of the aziridine ring in 3-bromo-1-alkyl-1-azoniatricyclo[2.2.1.02,6]heptane bromides by the action of various nucleophiles leads to formation of the corresponding 6-substituted 2-alkyl-2-azabicyclo[2.2.1]heptanes.     

Symmetry specified enumeration of substituted derivatives: an easy solution to the complex problem

Several sophisticated methods to solution of symmetry specified enumeration problems are available in the modern literature. In this paper we propose a simple technique that allows one to manually compute the exact numbers of fixed-symmetry derivatives for a given structure either with inclusion or ignoring the substitution patterns. The basic idea of the method suggested consists in the derivation of Pólya-like cycle indices for the automorphism groups of specially constructed orbit partition graphs; the expansion of these indices and subsequent simple calculations result in the desired numbers of substituted derivatives with achiral substituents. Limitations of the new technique (and a method suggested earlier) depend on the relevance of the orbit partitions for particular subgroups of the point symmetry group. For illustration purposes, the results obtained for the prismane (D _3h ) and adamantane (T _d ) structures are discussed. In the former case the numbers of substituted derivatives can be found for all subgroups of the D _3h group, whereas in the latter case these numbers can be determined for eight out of eleven subgroups of the T _d point symmetry group. This work is based on the text of the lecture presented by the authors at the 5th All-Russia Conference on Molecular Modeling (Moscow, April 2007). The paper deals with the methodology and detailed treatment of applied aspects related to solution of enumeration problems for substituted derivatives with prescribed symmetry groups. Unlike the known methods of symmetry specified enumeration, the technique suggested is simple enough and may be regarded as generalization of the Pólya methodology, which is widely used by chemists. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 227–245, February, 2008.     

Synthesis of 3,6-dialkyl-4,5-dihydro-4,5-dichloro-2,1-benzisoxazoles from o-nitrophenylcyclopropanes

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 130–131, January, 1992.