Synthesis,structure, and antimicrobial activity of (carboxyalkyl)dimethylsulfonium halides

Reactions of a series of ω-halocarboxylic acids (2-bromo-, 2-chloroethanoic, 3-bromo- and 3-chloropropanoic) with dimethyl sulfide resulted in the formation of stable (carboxylalkyl)dimethylsulfonium bromides and chlorides. Composition and structure of the salts obtained were established by a complex of chemical, physical and physicochemical methods. The sulfonium salts obtained showed high antibacterial and antimycotic activities with respect to the pathogenic microflora of humans and animals.     

Erratum to: Synthesis and Biological Activity of New Aminophosphabetaines

Russian Journal of General Chemistry - Erratum     

Reactions of Triphenylphospine with ω-Bromoalkanecarboxylic Acids

Russian Journal of General Chemistry - Phosphonium salts and their corresponding phosphabetaines—ω-phosphonioalkanoates—with a large number of methylene units were obtained on the...     

Photochemical Reactions of Regioisomeric 2,2‐Dimethyl‐5,5‐diphenyl‐ and 5,5‐Dimethyl‐2,2‐diphenyl‐Substituted Diazo Ketones of a Tetrahydrofuran Series

The principal direction of conventional photolysis of the regioisomeric 2,2‐dimethyl‐5,5‐diphenyl‐ and 5,5‐dimethyl‐2,2‐diphenyl‐substituted 4‐diazodihydrofuran‐3(2H)‐ones 1a and 1b , respectively, is the Wolff rearrangement, while other photochemical processes, which are giving rise to the formation of C? H‐insertion, 1,2‐alkyl‐ or ‐aryl‐shifts, as well as H‐atom‐abstraction products occur to a much lower degree (Schemes 2 and 3). The ratio of similar reaction products from both regioisomers 1a and 1b is essentially independent of their structure, and a substantial effect of the relative position of the Ph and diazo group to each other on the yield of C? H‐insertion products does not occur. Based on stereochemical considerations, the Wolff rearrangement of diazodihydrofuran‐3(2H)‐ones apparently proceeds in a concerted manner, whereas the appearance in the reaction mixture of 1,2‐shift and H‐atom‐abstraction products points to the parallel generation during photolysis of singlet and triplet carbenes (Schemes 4 and 5).     

Reactions of 5,7-Dichloro-4,6-dinitrobenzofuroxane and -furazane with Triphenylphosphine

Reactions of 5,7-dichloro-4,6-dinitrobenzofuroxane and 5,7-dichloro-4,6-dinitrobenzofurazane with triphenylphosphine proceed through a nucleophilic aromatic substitution of chlorine and nitro groups in the sixmembered ring of the heterocycles. The structure of the phosphorylation products was established from the IR, ³¹P NMR, and mass spectra and from XRD and elemental analysis. Schemes of the routes of the phosphorylation are discussed.     

Structure and Ion-Selective Properties of 2-Phosphorylphenols

The structure and ion-selective properties of some 2-phosphorylphenols were studied. It was shown that, irrespective of the nature of the substituents on the benzene ring and on the phosphorus atom, these compounds exhibit potentiometric selectivity to cesium cation. The crystal structures of 2-(diphenylphosphoryl)-4-ethylphenol and 2-[(diphenylphosphoryl)methyl]phenol were established.     

Reactions of isocyanates with compounds containing active methylene groups in the presence of triethylamine

Compounds containing active methylene groups react with isocyanates of different structures in the presence of triethylamine to form functionally substituted amides. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2323–2330, October, 2005.     

Aza-Michael reaction as an efficient method for the synthesis of first representatives of β-azahetaryl-β-diphenylphosphorylalkanones

Aza-Michael reaction of (E)-4-(diphenylphosphoryl)but-3-en-2-one (1) with a number of mono-and bicyclic nitrogen heterocycles proceeds regioselectively in the absence of catalysts with the formation of corresponding β-azahetaryl β-diphenylphosphoryl ketones; in the case of imidazole, the presence of chiral organic catalysts allows one to increase the yields of the adducts and to obtain them in enantiomerically enriched form.

     

Effect of solvent,electronic, and steric factors on the reactivity of 1,1'-diethylferrocene, 1,1'-diacetylferrocene,and 1,1'-bis(diphenylphosphino)ferrocene towards hydrogen peroxide

The oxidation of Fc(C₂H₅)₂, Fc(COCH₃)₂, and Fc(PPh₂)₂, where Fc is a ferrocene, with hydrogen peroxide in aprotic (dioxane and acetonitrile) and hydroxyl-containing (ethanol, acetonitrile–water, and water) solvents is studied via electron spectroscopy. The reactivity of these metal complexes relative to an oxidant is due to the electron-donor or electron-acceptor properties of substituents, their sizes, and their capability for the specific solvation by a particular solvent. Possible mechanisms of the oxidation of metal complexes are discussed. When Fc(PPh₂)₂ is oxidized, the formation of ferrocenyl cation Fc⁺(PPh₂)₂ is due to the redox isomerism of ferrocenylphosphonium cation Fc(PPh₂)P⁺Ph₂, which can form during the reaction between protonated complex Fc(PPh₂)P(H⁺)Ph₂ and H₂O₂.