The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide
AbstractThe introduction and removal of protecting groups is ubiquitous in multi-step synthetic schemes. From a green chemistry standpoint, however, alternative strategies that employ in situ and reversible protection and deprotection sequences would be attractive. The reversible reactions of CO2 with amines could provide a possible vehicle for realizing this strategy. Herein, we present (1) the products of reaction of benzylamines with CO2 in a variety of solvents with and without the presence of basic additives; (2) new adducts associated with CO2 protected benzylamine in acetonitrile containing 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU); and (3) the intermolecular competitive acylation of benzylamine and benzyl alcohol and the intramolecular competitive acylation of (4-aminomethyl)phenyl) methanol with isopropenyl acetate in acetonitrile containing DBU in the absence and presence of CO2. View Full-Text
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Ethier, A.L.; Switzer, J.R.; Rumple, A.C.; Medina-Ramos, W.; Li, Z.; Fisk, J.; Holden, B.; Gelbaum, L.; Pollet, P.; Eckert, C.A.; Liotta, C.L. The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide. Processes 2015, 3, 497-513.
Ethier AL, Switzer JR, Rumple AC, Medina-Ramos W, Li Z, Fisk J, Holden B, Gelbaum L, Pollet P, Eckert CA, Liotta CL. The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide. Processes. 2015; 3(3):497-513.Chicago/Turabian Style
Ethier, Amy L.; Switzer, Jackson R.; Rumple, Amber C.; Medina-Ramos, Wilmarie; Li, Zhao; Fisk, Jason; Holden, Bruce; Gelbaum, Leslie; Pollet, Pamela; Eckert, Charles A.; Liotta, Charles L. 2015. "The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide." Processes 3, no. 3: 497-513.