1719-05-7Relevant articles and documents
Expeditious and practical synthesis of tertiary alcohols from esters enabled by highly polarized organometallic compounds under aerobic conditions in Deep Eutectic Solvents or bulk water
Quivelli, Andrea F.,D'Addato, Giovanna,Vitale, Paola,García-álvarez, Joaquín,Perna, Filippo M.,Capriati, Vito
, (2021/01/18)
An efficient protocol was developed for the synthesis of tertiary alcohols via nucleophilic addition of organometallic compounds of s-block elements (Grignard and organolithium reagents) to esters performed in the biodegradable choline chloride/urea eutectic mixture or in water. This approach displays a broad substrate scope, with the addition reaction proceeding quickly (20 s reaction time) and cleanly, at ambient temperature and under air, straightforwardly furnishing the expected tertiary alcohols in yields of up to 98%. The practicability of the method is exemplified by the sustainable synthesis of some representative S-trityl-L-cysteine derivatives, which are a potent class of Eg5 inhibitors, also via telescoped one-pot processes.
P-Iodinations in hydrocarbon media: Continuous flow reactor application
Slocum,Tekin, Kristen C.,Nguyen, Quang,Whitley, Paul E.,Reinscheld, Thomas K.,Fouzia, Begum
experimental part, p. 7141 - 7145 (2012/01/05)
Regiospecific iodination of aryl amines, that is, aryl compounds possessing strong electron donating groups (EDG's) in the p-position, is described. This procedure features not only the unique use of hydrocarbon media for such substitutions but also the absence of any oxidants aside from iodine itself. Further potential of this hydrocarbon media based electrophilic aromatic substitution is demonstrated by the coupling of the iodination with an in situ halogen/lithium exchange and product forming nucleophilic addition in a batch process. The protocol was ultimately scaled to a continuous flow reactor using an isolated p-iodoarylamine. Constituted as described, these procedures possess enhanced atom-economical, green and safety aspects compared to existing literature protocols.
Electrophilicity versus electrofugality of tritylium ions in aqueous acetonitrile
Horn, Markus,Mayr, Herbert
supporting information; scheme or table, p. 7478 - 7487 (2010/08/20)
First-order rate constants kw for the reactions of a series of donorsubstituted triphenylmethylium (tritylium) ions with water in aqueous acetonitrile have been determined photometrically at 20°C using stopped-flow and laser-flash techniques. T
CONDITIONS FOR THE APPLICATION OF ELECTROSTATIC THEORY TO THE KINETICS OF THE REACTIONS OF CONJUGATED CARBONIUM IONS WITH ANIONS IN MIXED AQUENOUS ORGANIC SOLVENTS
Sinev, V. V.,Nikolova, T. A.
, p. 528 - 530 (2007/10/02)
On the basis of an analysis of data on the kinetics of the reaction of conjugated cations of the triarylmethane series with various anions in mixed aquenous organic solvents it was shown that the deviations from electrostatic theory observed for the kinetics of the reactions of cationic substrates with OH- anion are due to transsolvation of the reaction center and to competition from the relay mechanism of transfer of the hydroxide ion with direct nucleophilic displacement of the water from the hydrate shell of the cation.
