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Processes 2015, 3(3), 497-513; doi:10.3390/pr3030497

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
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Michael Henson
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)
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Abstract

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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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.

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