134022-41-6Relevant articles and documents
A mild and efficient procedure for alkenols oxyselenocyclization by using ionic liquids
Kosti?, Marina,Verdía, Pedro,Fernández-Stefanuto, Verónica,Puchta, Ralph,Tojo, Emilia
supporting information, (2019/01/08)
A mild and efficient procedure for the oxyselenocyclization of unsaturated alcohols by treatment with phenylselenyl chloride using ionic liquids as solvents/catalyzers has been developed. The reaction proceeds instantaneously under mild conditions with ab
Kinetic and mechanistic studies of base-catalyzed phenylselenoetherification of (Z)- and (E)-Hex-4-en-1-ols
Divac, Vera M.,Puchta, Ralph,Bugarcic, Zorica M.
experimental part, p. 7783 - 7790 (2012/09/11)
The mechanism of phenylselenoetherification of (Z)- and (E)-hex-4-en-1-ols using some bases (triethylamine, pyridine, quinoline, 2,2′-bipyridine) as catalysts and some solvents [tetrahydrofuran (THF) and CCl4] as reaction media was examined through studies of kinetics of the cyclization by UV-vis spectrophotometry. It was demonstrated that the intramolecular cyclization is facilitated in the presence of bases as a result of the hydrogen bond between the base and the alkenol's OH group. The rate constants in the base-catalyzed reactions are remarkably influenced by the bulkiness and basicity of the base used and the nature of the considered nitrogen donors. The obtained values for rate constants show that the reaction with triethylamine is the fastest one. THF with higher polarity and higher basic character is better as a solvent than CCl4. Quantum-chemical calculations [MP2(fc)/6- 311+G**//B3LYP/6-311+G** + ZPE(B3LYP/6- 311+G**] show that the cyclization of (Z)-hex-4-en-1-ol to a tetrahydrofuranoid five-membered ring is kinetically controlled, while the cyclization of (E)-hex-4-en-1-ol to the tetrahydropyranoid six-membered ring is thermodynamically controlled. This is in accordance with previous experimental findings.
Regio- and stereoselectivity in phenylselenoetherification of (Z)- and (E)-hex-4-en-1-ols
Divac, Vera M.,Bugarcic, Zorica M.
experimental part, p. 3684 - 3688 (2010/03/25)
Δ4-Primary alkenols (Z)- and (E)-hex-4-en-l-ols underwent facile cyclization to the corresponding phenyl selenoethers using PhSeX (X = Cl, Br) in high yields and in good to excellent selectivities in the presence of some catalysts (Lewis acids
Rapid SnCl2 catalyzed phenylselenoetherification of (Z)- and (E)-hex-4-en-1-ols
Divac, Vera M.,Rvovic, Marina D.,Bugarcic, Zorica M.
experimental part, p. 1373 - 1376 (2009/12/08)
A fast and efficient method for intramolecular heterocyclization of (Z)- and (E)-hex-4-en-1-ols was developed. The method does not cause side reactions of the substrates and provides the cyclic phenylselenoethers in high yields after only few minutes. A c
Molecular orbital study of the rearrangement of seleniranium ions
Markovic, Zoran,Konstantinovic, Stanimir,Juranic, Ivan,Dosen-Micovic, Ljiljana
, p. 429 - 434 (2007/10/03)
The mechanism of phenylselenoetherification of unsaturated alcohols, involving seleniranium cationic intermediates, is studied by the semiempirical molecular-orbital MNDO-PM3 method.Results of calculation on several Δ4-alkenols attacked by PhSe
Regioselectivity in Cyclofunctionalization of Olefinic Alcohols with Benzeneselenenyl Halides at Different Temperatures
Konstantinovic, Stanimir,Bugarcic, Zorica,Milosavljevic, Slobodan,Schroth, Gerhard,Mihailovic, Mihailo Lj.
, p. 261 - 268 (2007/10/02)
The regioselectivity in cyclofunctionalization of some acyclic olefinic alcohols with benzeneselenenyl halides (PhSeCl and PhSeBr) at different temperatures (-78 deg C, 0 deg C and room temperature) is investigated.It has been found that Δ4- and Δ5-alkenols are converted into five- and/or six-membered cyclic phenyl selenoethers, the yield of which decreases with increasing temperature.PhSeCl has been found to be more efficient than PhSeBr in the cyclization reactions. Key Words: Olefinic alcohols / Cyclofunctionalization / Benzeneselenenyl halides
Electrochemical cyclization of unsaturated hydroxy compounds. Phenylselenoetherification and phenylselenolactonization
Vukicevic,Konstantinovic,Mihailovic
, p. 859 - 865 (2007/10/02)
Phenylselenoetherification and phenylselenolactonization were performed in one step by electrolysis of unsaturated alcohols or carboxylic acids and diphenyl diselenide in organic solvent containing halide ions as mediators.
