143589-31-5Relevant academic research and scientific papers
A microwave-assisted deconjugative esterification of α,β- unsaturated carboxylic acids through α,β-unsaturated ketene intermediates
Sano, Shigeki,Ichikawa, Takashi,Nakao, Michiyasu,Nagao, Yoshimitsu
experimental part, p. 68 - 69 (2012/03/11)
A facile synthetic approach to β,γ-unsaturated esters by deconjugative esterification of α,β-unsaturated carboxylic acids with alcohols in the presence of 1,3-dicyclohexylcarbodiimide (DCC), Me 3N·HCl, and Me2NEt is described. The on
Microwave-assisted regioselective olefinations of cyclic mono- and di-ketones with a stabilized phosphorus ylide
Wu, Jinlong,Li, Dan,Wu, Huafeng,Sun, Lijie,Dai, Wei-Min
, p. 4643 - 4650 (2007/10/03)
A number of cyclic mono- and di-ketones underwent regioselective olefination with (carbethoxyethylidene)triphenylphospharane under controlled microwave heating. The Wittig reaction of 4-substituted cyclohexanones or 1,2- and 1,4-cyclohexanediones with the ylide at 190 °C for 20 min in MeCN afforded the exocyclic olefins in >94:6 isomer ratios. On the other hand, the same reactions carried out at 230 °C for 20 min in the presence of 20 mol % DBU furnished the endocyclic olefins in >83:17 isomer ratios. The base-mediated isomerization of the exocyclic olefins into the endocyclic isomers was primarily driven by thermodynamic stability of the products and the effect of ring structures on deconjugation was examined.
Novel deconjugative esterification of 2-cyclohexylideneacetic acids through 4-(pyrrolidin-1-yl)pyridine-catalyzed carbodiimide couplings
Sano, Shigeki,Harada, Etsuko,Azetsu, Tomohiro,Ichikawa, Takashi,Nakao, Michiyasu,Nagao, Yoshimitsu
, p. 1286 - 1287 (2008/02/05)
4-(Pyrrolidin-1-yl)pyridine-catalyzed deconjugative esterification of 2-cyclohexylideneacetic acids afforded isopropyl 2-(cyclohex-1-enyl)acetate by employing 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride as a coupling reagent. On the other
Highly regioselective Wittig reactions of cyclic ketones with a stabilized phosphorus ylide under controlled microwave heating
Wu, Jinlong,Wu, Huafeng,Wei, Shaoyong,Dai, Wei-Min
, p. 4401 - 4404 (2007/10/03)
Significant base and temperature effects on the Wittig reactions of cyclohexanones with (carbethoxymethylene)triphenylphosphorane under microwave irradiation were observed. For the Wittig reactions carried out in a domestic microwave oven under solvent-free conditions, the initially formed exo-olefin products isomerized into the thermodynamically more stable endo-olefins due to uncontrolled high reaction temperature. In sharp contrast, under controlled microwave heating, both exo- and endo-olefins have been selectively synthesized by accurately regulating the reaction temperature with or without a base.
