4412-46-8Relevant academic research and scientific papers
Reaction of Catalytic Olefination of Hydrazones with Polyhaloalkanes. Investigation of Alkene Formation Chemoselectivity
Korotchenko,Shastin,Nenaidenko,Balenkova
, p. 527 - 531 (2003)
Hydrazones of carbonyl compounds at treatment with polyhaloalkanes in the presence of CuCl as catalyst are converted into substituted alkenes with formation of a new C=C bond.
Transition metal free large-scale synthesis of aromatic vinyl chlorides from aromatic vinyl carboxylic acids using bleach
Hatvate, Navnath T.,Takale, Balaram S.,Ghodse, Shrikant M.,Telvekar, Vikas N.
supporting information, p. 3892 - 3894 (2018/10/02)
While continuing our research on Hunsdiecker reaction, we came across an interesting application of bleach, sodium hypochlorite (NaOCl) for decarboxylative chlorination reaction. The reaction is easily scaled up to 10 mmol. The reaction has good tolerance towards wide variety of functional groups. The reaction has mild conditions and gave relatively high chemical yield of the desired product.
Catalytic olefination. Estimation of the reactivity of polyhaloalkanes
Nenaidenko,Korotchenko,Shastin,Tyurin,Balenkova
, p. 1750 - 1756 (2007/10/03)
Global electrophilicity indices and carbon-halogen bond energies of a wide series of halogen derivatives were calculated in terms of the density functional theory (DFT). The calculated values were used to estimate the reactivity of halogen derivatives under conditions of catalytic olefination. Reactions of N-unsubstituted hydrazones with polyhaloalkanes in the presence of CuCl afforded substituted alkenes. The relation between the structure of polyhaloalkanes and their reactivity was studied using the reaction with 4-chlorobenzaldehyde hydrazone as an example. It was found that increase in the global electrophilicity index and decrease in the C-Hlg bond energy are accompanied by increase in the olefinating power of halogen derivatives.
Catalytic olefination reaction of carbonyl compounds. A study on stereoselectivity of alkene formation
Nenaidenko,Korotchenko,Shast,Tyur,Balenkova
, p. 1835 - 1840 (2007/10/03)
The mechanism of formation of alkene stereoisomers in the catalytic olefination reaction of carbonyl compounds was studied. 4-Chlorobenzaldehyde hydrazone 1 stereoselectively reacts with a number of F-, Cl-, Br-, and I-containing polyhaloalkanes in the presence of catalytic amounts of CuCl to give ω-substituted styrenes 2 with the more thermodynamically stable alkene isomer being the major product. A model for the formation of the stereoisomers of alkenes 2 in the olefination reaction is proposed. Stereoselectivity of the reaction is determined by elimination of copper(II) halides from the lowest-lying conformers of organocopper intermediates II. According to quantum-chemical calculations, the elimination should involve the staggered conformations with antiperiplanar arrangement of C-Hal and C-Cu bonds and proceed by the E2 anti-elimination mechanism. The results of quantum-chemical calculations are in good agreement with the experimental E/Z alkene isomer ratios.
Synthesis of 3-Substituted Indolizines from the Reaction of Chlorocarbenes with 2-Vinylpyridine
Bonneau, Roland,Romashin, Yuri N.,Liu, Michael T. H.,MacPherson, Spenser E.
, p. 509 - 510 (2007/10/02)
3-Substituted indolizines have been obtained in a one-step procedure from the reaction of chlorocarbenes with 2-vinylpyridine.
Thermolysis and Photolysis of 3-Chloro-3-benzyldiazirines in Alkenes: Evidence for a Carbene-Alkene Complex
Liu, Michael T. H.,Soundararajan, N.,Paike, N.,Subramanian, R.
, p. 4223 - 4227 (2007/10/02)
Photolysis and thermolysis of substituted 3-chloro-3-benzyldiazirines in alkenes yielded cyclopropanes and chlorostyrenes as products.The results suggest that the cyclopropanation of benzylchlorocarbenes is independent of substituents.However, 1,2-hydrogen migration is accelerated by OCH3 or CH3 substituents, and is decelerated by a Cl substituent on the phenyl ring.These results support the existence of an energy barrier to 1,2-H migration.Evidence is provided for carbene-alkene complexation.
