14251-72-0Relevant articles and documents
Organic synthesis in soft wall-free microreactors: Real-time monitoring of fluorogenic reactions
Marchand,Dubois,Delattre,Vinet,Blanchard-Desce,Vaultier
, p. 6051 - 6055 (2008/12/22)
A new approach of "laboratory on a chip" (LOC) devoted to organic synthesis based on electrically operated ionic liquid microdroplets used as air-stable "soft" microreactors was recently introduced. A number of challenging issues have yet to be addressed
Reaction rates as a function of scale within ionic liquids: Microscale in droplet microreactors versus macroscale reactions in the case of the grieco three-component condensation reaction
Dubois, Philippe,Marchand, Gilles,Gmouh, Said,Vaultier, Michel
, p. 5642 - 5648 (2008/02/13)
Task-specific ionic liquids (TSILs) and more specifically binary task-specific ionic liquids (BTSILs), a unique subclass, have been shown to be excellent supports for solution-phase chemistry. The negligible volatility of ionic liquids enables their use a
Ionic liquid droplet as e-microreactor
Dubois, Philippe,Marchand, Gilles,Fouillet, Yves,Berthier, Jean,Douki, Thierry,Hassine, Fatima,Gmouh, Said,Vaultier, Michel
, p. 4909 - 4917 (2008/02/12)
A powerful approach combining a droplet-based, open digital microfluidic lab-on-a-chip using task-specific ionic liquids as soluble supports to perform solution-phase synthesis is reported as a new tool for chemical applications. The negligible volatility of ionic liquids enables their use as stable droplet reactors on a chip surface under air. The concept was validated with different ionic liquids and with a multicomponent reaction. Indeed, we showed that different ionic liquids can be moved by electrowetting on dielectric (EWOD), and their displacement was compared with aqueous solutions. Furthermore, we showed that mixing ionic liquids droplets, each containing a different reagent, in "open" systems is an efficient way of carrying supported organic synthesis. This was applied to Grieco's tetrahydroquinolines synthesis with different reagents. Analysis of the final product was performed off-line and on-line, and the results were compared with those obtained in a conventional reaction flask. This technology opens the way to easy synthesis of minute amounts of compounds ad libitum without the use of complex, expensive, and bulky robots and allows complete automation of the process for embedded chemistry in a portable device. It offers several advantages, including simplicity of use, flexibility, and scalability, and appears to be complementary to conventional microfluidic lab-on-a-chip devices usually based on continuous-flow in microchannels.
POLAR RADICALS XVIII. ON THE MECHANISM OF CHLORINATION BY N-CHLOROAMINES: INTERMOLECULAR AND INTRAMOLECULAR ABSTRACTION.
Tanner, Dennis D.,Arhart, Richard,Meintzer, Christian P.
, p. 4261 - 4278 (2007/10/02)
The photochlorinations of the n-butyl, n-pentyl, and n-hexyltrimethylammonium chlorides, using molecular chlorine in hexachloroacetone or 15percent CD3CO2D/85percent H2SO4, or using N-chlorodimethylamine in the acid solvent are described.The ammonium group exerted a strong polar directing effect upon the site of substitution.This effect was found to be more pronounced in the more polar protic solvent.The reagent, N-chlorodimethylamine, generated the dimethylamminium radical, whose reaction showed a polar sensitivity toward hydrogen abstraction similar to that of the chlorine atom, but exhibiting a much greater secondary/primary selectivity.Comparison of the isomer distributions obtained from the self photochlorination reactions of N-chloro-n-hexylmethylamine and N-chloro-n-pentylmethylamine in the acid solvent, with the distribution pattern obtained for the chlorinations of the ammonium salts with N-chlorodimethylamine, suggested that the self chlorinations of the N-chloroamines proceed by the intramolecular hydrogen abstraction mechanism suggested previously.