期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 13, 页码 4648-4651出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo100783v
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资金
- Biotechnology and Biological Sciences Research Council [BB/C50446X/1]
- Engineering and Physical Sciences Research Council
- University of Birmingham
- Biotechnology and Biological Sciences Research Council [BB/C50446X/1] Funding Source: researchfish
The synthesis of a new photolabile protecting group for carboxylic acids, alpha-carboxy-6-nitroveratryl (alpha CNV), 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.
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