[reaction: see text] 2-Nitrobenzyl enol ethers, when photolyzed in the presence of air, result in an oxidative C=C bond scission, forming a ketone as the major product (>60% yield). Enol release leads to the aldehyde as the minor product.
[reaction: see text] A new photoremovable protecting group for carboxylic acids is introduced. The protecting group 1-[2-(2-hydroxyalkyl)phenyl]ethanone, HAPE, is used to protect various carboxylic acids. When photolyzed, the protected compound releases the acid in 70-85% isolated yields. The synthesis and the results of photorelease of the protected acids are presented here.
Deprotection Deprotection O 0345 1-[2-(2-Hydroxyalkyl)phenyl]ethanone: A New Photoremovable Protecting Group for Carboxylic Acids. -The synthesis of a novel photoremovable protecting group for carboxylic acids is described. When photolyzed the protected compounds (V) release the acids (IV) in 70-85% isolated yield. -(ATEMNKENG, W. N.; LOUISIANA, L. D. I.; YONG, P. K.; VOTTERO, B.; BANERJEE*, A.; Org. Lett. 5 (2003) 23, 4469-4471; Dep. Chem., Univ. N. Dak., Grand Forks, ND 58202, USA; Eng.) -M. Paetzel 12-071
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