- Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity.
Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity.
Organic & biomolecular chemistry (2012-09-15)
Azarmidokht Gholamipour-Shirazi, Christian Rolando
PMID22976369
ABSTRACT
We describe here the determination of the alkylation rate of a set of organic superbases by iodomethane in DMF using a microfluidic continuous flow reactor. Surprisingly, log k(Alkylation) follows the inverse trend of pK(BH+) of the base. Mayr's equation allows a more quantitative approach. From a synthetic point of view, TMGN and BEMP are demonstrated to be the best choices.
MATERIALS
Product Number
Brand
Product Description
Sigma-Aldrich
Iodomethane solution, 2.0 M in tert-butyl methyl ether, contains copper as stabilizer
Supelco
Iodomethane solution, certified reference material, 2000 μg/mL in methanol: water (4:1)