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  • Title: Photorelease of alcohols from 2-nitrobenzyl ethers proceeds via hemiacetals and may be further retarded by buffers intercepting the primary aci-nitro intermediates.
    Author: Hellrung B, Kamdzhilov Y, Schwörer M, Wirz J.
    Journal: J Am Chem Soc; 2005 Jun 29; 127(25):8934-5. PubMed ID: 15969554.
    Abstract:
    The mechanism for the photoinduced release of glycolic acid from its 2-nitrobenzyl ether was reinvestigated. The pH-dependent rate constants of the thermal reactions initiated by irradiation are similar to those reported previously for 2-nitrobenzyl methyl ether. A hemiacetal intermediate that limits the release rate of glycolic acid at pH values </=7 was identified by time-resolved IR and UV measurements. Furthermore, 2-(2'-nitrosophenyl)-1,3-dioxolan-4-one, a long-lived intermediate formed by intramolecular trapping of the aci-tautomer, was observed and characterized.
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