The Effects of Solvent and Added Bases on the Protection of Benzylamines with Carbon Dioxide
| Autor: | Charles L. Liotta, Pamela Pollet, Wilmarie Medina-Ramos, Charles A. Eckert, Amber C. Rumple, Jason S. Fisk, Bruce S. Holden, Zhao Li, Leslie T. Gelbaum, Jackson R. Switzer, Amy L. Ethier |
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| Rok vydání: | 2015 |
| Předmět: |
Green chemistry
Process Chemistry and Technology carbamate carbon dioxide Bioengineering protection lcsh:Chemical technology Reversible reaction lcsh:Chemistry Isopropenyl acetate Acylation chemistry.chemical_compound Benzylamine amine lcsh:QD1-999 chemistry Benzyl alcohol Chemical Engineering (miscellaneous) Organic chemistry lcsh:TP1-1185 sustainable Methanol Acetonitrile |
| Zdroj: | Processes, Vol 3, Iss 3, Pp 497-513 (2015) Processes Volume 3 Issue 3 Pages 497-513 |
| ISSN: | 2227-9717 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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