6824-60-8Relevant academic research and scientific papers
Polyelectrolyte-catalyzed Diels–Alder reactions
Pothanagandhi, Nellepalli,Sivaramakrishna, Akella,Vijayakrishna, Kari
, p. 132 - 136 (2016/08/05)
Imidazolium-based poly(ionic liquids) bearing bromide and bis(trifluoromethane)sulfonimide as counteranions [poly(ViEIm)Br and poly(ViEIm)NTf2] derived from reversible addition fragmentation chain transfer (RAFT) polymerization techniques are u
Microwave-assisted aza-Prins reaction. Part 1: Facile preparation of natural-like 3-azabicyclo[3.3.1]non-6-enes
Parchinsky, Vladislav,Shumsky, Alexei,Krasavin, Mikhail
, p. 7157 - 7160 (2012/01/04)
A facile and operationally simple route to diastereomerically pure, natural-like 3-azabicyclo[3.3.1]non-6-enes via microwave-assisted, BF 3·OEt2-promoted aza-Prins reaction has been developed. Complexity-generating transformations based on these products involving reactive functionalities introduced during the aza-Prins step have been developed.
Diels-Alder reactions in pyridinium based ionic liquids
Xiao, Ying,Malhotra, Sanjay V.
, p. 8339 - 8342 (2007/10/03)
Diels-Alder reactions have been investigated in pyridinium based ionic liquids. These solvents are found to be more effective compared to the organic solvent studied, in enhancing the reaction rate and product yields. Recycled ionic liquids also gave exce
Phosphonium tosylates as solvents for the Diels-Alder reaction
Ludley, Petra,Karodia, Nazira
, p. 2011 - 2014 (2007/10/03)
Phosphonium tosylates have been investigated as solvents for the Diels-Alder reactions of isoprene with methyl acrylate, but-3-en-2-one and acrylonitrile. The reactions with oxygen-containing dienophiles showed high regioselectivity.
Solvent effects on Diels-Alder reactions. the use of aqueous mixtures of fluorinated alcohols and the study of reactions of acrylonitrile
Cativiela, Carlos,Garcia, Jose I.,Gil,Martinez, Rosa M.,Mayoral, Jose A.,Salvatella, Luis,Urieta, Jose S.,Mainar,Abraham, Michael H.
, p. 653 - 660 (2007/10/03)
Rate, endolexo, regio- and diastereo-facial selectivities of several Diels-Alder reactions were measured in a series of fluorinated alcohol-water mixtures, whose solvophobicity has been determined by means of the solvophobic power (Sp) parameter. Solvophobicity is the main factor influencing the reaction rate, although in some reactions hydrogen bond donating (HBD) ability may also play a role. Both solvophobicity and HBD ability are important to account for changes in endolexo selectivity. HBD ability is the main factor responsible for the changes in regio- and diastereo-facial selectivities, induced by the reaction medium. On the other hand, the kinetic rate constants and endolexo selectivity of the reaction of acrylonitrile with cyclopentadiene, as well as the regioselectivity of the reaction of acrylonitrile with isoprene, have been determined in 23 reaction media. The analysis of the results using empirical solvent parameters show that the reaction rate depends on solvophobic, HBD and dipolarity interactions, whereas endolexo selectivity is influenced by solvophobic and dipolarity interactions, and the regioselectivity only by HBD effects.
Evidence for 2-Hexene-1,6-diyl Diradicals Accompanying the Concerted Diels-Alder Cycloaddition of Acrylonitrile with Nonpolar 1,3-Dienes
Li, Yufei,Padias, Anne Buyle,Hall, H. K.
, p. 7049 - 7058 (2007/10/02)
The spontaneous reactions of a series of alkyl 1,3-dienes with acrylonitrile (AN) were investigated.Reproducible spontaneous copolymerizations were shown to compete with the expected concerted cycloadditions.For dienes which exist in s-cis/s-trans equilibrium, both copolymer and cycloadduct are formed.Kinetic measurements show that the alternating copolymerization and cycloaddition are two independent paralell second order reactions.With 1,3-cyclohexadiene and 1,2-dimethylenecyclohexane, for which s-gauche is in equilibrium with s-cis, copolymerization still competes with cycloaddition.The s-trans-locked verbenene forms only copolymer, while s-cis-locked cyclopentadiene and 1,2-dimethylenecyclopentane form only cycloadduct rapidly.Our explanation involves a 2-hexene-1,6-diradical, formed by combination between the terminal carbons of the s-gauche or s-trans diene and acrylonitrile.This does not cyclize but initiates copolymerization.Competitively s-cis conformer undergoes classical concerted addition.
