Journal of Organic Chemistry 2003-11-14

Model compounds of caged capsaicin: design, synthesis, and photoreactivity.

Alan R Katritzky, Yong-Jiang Xu, Anatoliy V Vakulenko, Allan L Wilcox, Keith R Bley

Index: J. Org. Chem. 68(23) , 9100-4, (2003)

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Abstract

Molecules were prepared with substituted nitrobenzyl groups covalently bonded to N-(4-hydroxy-3-methoxybenzyl)acetamide (2) by ether or carbonate linkages. These compounds decomposed under irradiation at 363 nm. Those with carbonate linkages decomposed at slower rates than those with ether linkages. Molecules with dimethoxy-substituted benzyl groups decomposed more slowly than monomethoxy-substituted benzyl groups due to the electronic characteristics of the benzylic carbon.