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The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide

1
School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, GA 30332-0400, USA
2
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332-0400, USA
3
Dow Chemical Company, Midland, MI 48674, USA
4
Specialty Separations Center, Georgia Institute of Technology, Atlanta, GA 30332-0400, USA
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Michael Henson
Processes 2015, 3(3), 497-513; https://doi.org/10.3390/pr3030497
Received: 20 May 2015 / Revised: 1 June 2015 / Accepted: 16 June 2015 / Published: 25 June 2015
(This article belongs to the Special Issue Sustainable Products and Processes)
The 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
Keywords: carbamate; amine; protection; carbon dioxide; sustainable carbamate; amine; protection; carbon dioxide; sustainable
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MDPI and ACS Style

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. https://doi.org/10.3390/pr3030497

AMA Style

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. https://doi.org/10.3390/pr3030497

Chicago/Turabian Style

Ethier, Amy L., Jackson R. Switzer, Amber C. Rumple, Wilmarie Medina-Ramos, Zhao Li, Jason Fisk, Bruce Holden, Leslie Gelbaum, Pamela Pollet, Charles A. Eckert, and Charles L. Liotta. 2015. "The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide" Processes 3, no. 3: 497-513. https://doi.org/10.3390/pr3030497

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