α-Carboxy-6-nitroveratryl: A Photolabile Protecting Group for Carboxylic Acids
| Autor: | Christopher W. Wharton, David Carteau, Maria-Eleni Ragoussi, Rui Ramalho, Dario M. Bassani, John S. Snaith, Alexander G. Russell |
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| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
Photolysis Molecular Structure Photochemistry Carboxylic acid Organic Chemistry Photodissociation Carboxylic Acids Quantum yield Alkylation Nitro Compounds Catalysis chemistry.chemical_compound chemistry Bromide Yield (chemistry) Quantum Theory Organic chemistry Spectrophotometry Ultraviolet Protecting group |
| Zdroj: | The Journal of Organic Chemistry. 75:4648-4651 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | The synthesis of a new photolabile protecting group for carboxylic acids, alpha-carboxy-6-nitroveratryl (alphaCNV), is described. Bromide 3, prepared in four steps from 3,4-dimethoxyphenylacetic acid, was used to alkylate carboxylic acids under mild conditions in good yield. Palladium-catalyzed deallylation afforded the acids 4a-h, which underwent rapid and quantitative photolysis at wavelengths longer than 300 nm to liberate the carboxylic acid in good to quantitative yield. The rate of photolysis and quantum yield were determined to be 325 s(-1) and 0.17. |
| Databáze: | OpenAIRE |
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