alpha-Carboxy-6-nitroveratryl: A Photolabile Protecting Group for Carboxylic Acids

AG Russell, ME Ragoussi, R Ramalho, Christopher Wharton, D Carteau, DM Bassani, John Snaith

Research output: Contribution to journalArticle

18 Citations (Scopus)


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.
Original languageEnglish
Pages (from-to)4648-4651
Number of pages4
JournalThe Journal of Organic Chemistry
Issue number13
Publication statusPublished - 1 Jul 2010


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