Organic letters

2, 5-Dimethylphenacyl as a new photoreleasable protecting group for carboxylic acids

P Klán, M Zabadal, D Heger

Index: Klan, Petr; Zabadal, Miroslav; Heger, Dominik Organic Letters, 2000 , vol. 2, # 11 p. 1569 - 1571

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Citation Number: 58

Abstract

The 2, 5-dimethylphenacyl chromophore, a new photoremovable protecting group for carboxylic acids, is proposed. Direct photolysis of various 2, 5-dimethylphenacyl esters in benzene or methanol at 254-366 nm leads to the formation of the corresponding carboxylic acids in almost quantitative isolated yields. The photodeprotection is based on efficient intramolecular hydrogen abstraction without the necessity of introducing a photosensitizer.