Composition and reactivity of aminolysis products of phenyl glycidyl ether with benzylamine

Composition of aminolysis products of phenyl glycidyl ether with benzylamine in various conditions was studied. The ratio of 1-(benzylamino)-3-phenoxypropan-2-ol and 1,1'-(benzylazanediyl)bis(3-phenoxypropan-2-ol) does not considerably depend on the nature of the solvent and is basically determined by ratio of initial reagents. 2,6-Bis(phenoxymethyl)morpholine was obtained by dehydration of aminodiol in conditions of Mitsunobu reaction with subsequent reductive debenzylation.     

Synthesis of Tetrahydrothiophene 1,1-Dioxides Fused to Oxazolidin-2-one and Morpholin-2-one Fragments

While developing methods of synthesis of sulfolanes fused through the C³–C⁴ bond to oxazolidin-2- one and morpholin-2-one fragments, the reactivity of cis- and trans-isomeric amino alcohols of the sulfolane series toward a number of cyclizing agents was studied. The cis isomers reacted with dimethyl acetylenedicarboxylate and triphosgene to afford the corresponding morpholin-2-ones and oxazolidin-2-ones, whereas the trans isomers gave rise to open-chain aminofumarates and urea derivatives, respectively. The reactions of both cis- and trans-amino alcohols with oxalic acid derivatives (diethyl oxalate, oxalyl chloride) led to the formation of exclusively acyclic mono- and/or diamides.     

New experimental results on the interference of the states of the hydrogen atom due to long-range interaction with the metal surface

The interference of the 2P state of the hydrogen atom due to unknown long-range interaction with the metal surface (Sokolov effect) has been studied by an atomic interferometer. In contrast to previous experiments, where an atomic beam passed through slits in metal plates, a beam in the presented experiments passes at a given distance from the edges of the plates. It has been found that the interference is clearly observed if two plates are located on the same side of the beam. However, this interference disappears if one plate is displaced to the opposite side. This result cannot be explained in the framework of the available hypotheses on the nature of the effect under investigation.     

Cage-like amino alcohols. synthesis, reactions, and application

The review analyzes methods for the synthesis of amino alcohols containing cage-like norbornene, norbornane, and adamantane fragments. Such reactions of amino alcohols as selective functionalization of hydroxy and amino groups, as well as heterocyclizations with formation of nitrogen- and oxygen-containing heterocycles, are considered. Biological activity of cage-like amino alcohols and their derivatives and their use as ligands in catalytic asymmetric syntheses are discussed.     

Synthesis, structure, and transformations of N-(bicyclo[2.2.1]hept-5-en-endo-2-ylmethyl)-N-[(oxiran-2-yl) methyl]-arenesulfonamides

Reaction of N-(bicyclo[2.2.1]hept-5-en-endo-2-ylmethyl)arenesulfonamides with epichlorohydrin in the presence of tetramethylammonium iodide afforded a group of framework N-[(oxiran-2-yl)methyl]sulfonamides and also a series of new dioxiranes, N-(oxiran-2-yl)methyl-N-(exo-5,6-epoxybicyclo[2.2.1]heptan-endo-2-ylmethyl)arenesulfonamides. The aminolysis of N-(oxiran-2-yl)methyl]arenesulfonamides with benzylamine and benzylpiperazine led to the chemo- and regioselective opening of the epoxy ring according to Krasusky rule. The structure of compounds was established by spectral methods and the XRD analysis.     

Experimental and theoretical study on the reaction of bicyclo[2.2.1]hept-5-en-endo-2-ylmethanamine with glycidyl ethers

Reactions of bicyclo[2.2.1]hept-5-en-endo-2-ylmethanamine with phenyl, 4-methylphenyl, 3-methylphenyl, 2-methylphenyl, 4-methoxyphenyl, cyclohexyl, and cyclohexenyl 2,3-epoxypropyl ethers gave the corresponding N-mono- and N,N-bis(3-R-oxy-2-hydroxypropyl) derivatives. The structure of the newly synthesized amino alcohols and regioselectivity of oxirane ring opening were determined by IR spectroscopy, ¹H and ¹³C NMR, and mass spectrometry. The reaction mechanism was studied by quantum chemistry at the PCM/B3LYP/6-31G(d) level of theory.     

Five-membered oxaza heterocyclic compounds on the basis of epoxides and aziridines

The review summarizes methods for the synthesis of 1,3-oxazolidin-2-ones, 1,3-oxazolidines, and dihydro-1,3-oxazoles from epoxides and aziridines. Possible applications of N,O-containing heterocycles in medicinal and organic chemistry as biologically active substances and intermediate products for their preparation are considered.     

Fine-structure effects in relativistic calculations of the static polarizability of the helium atom

We use the relativistic configuration-interaction method and the model potential method to calculate the scalar and tensor components of the dipole polarizabilities for the excited states 1s3p ³ P ₀ and 1s3p ³ P ₂ of the helium atom. The calculations of the reduced matrix elements for the resonant terms in the spectral expansion of the polarizabilities are derived using two-electron basis functions of the relativistic Hamiltonian of the atom, a Hamiltonian that incorporates the Coulomb and Breit electron-electron interactions. We formulate a new approach to determining the parameters of the Fuss model potential. Finally, we show that the polarizability values are sensitive to the choice of the wave functions used in the calculations. Zh. éksp. Teor. Fiz. 115, 494–504 (February 1999)     

Experimental and theoretical study of the reaction between bicyclo[2.2.1]hept-5-en-endo-2-ylmethylamine and 2-[(2-allylphenoxy)methyl]oxirane

In reactions of bicyclo[2.2.1]hept-5-en-endo-2-ylmethylamine with 2-[(2-allylphenoxy)methyl]oxirane alongside the product of amine monoalkylation a compound was obtained and isolated by chromatography on silica gel resulting from the reaction of the monoalkylated substance with the initial epoxide. The structure of new aminoalcohols and the regiochemistry of the oxirane opening were examined using IR, 1H NMR, and mass spectra. The features of the reaction mechanism were considered applying quantum-chemical calculations in the level of theory PCM/B3LYP/6-3aG(d).