Journal article
Photorelease of alcohols from 2-nitrobenzyl ethers proceeds via hemiacetals and may be further retarded by buffers intercepting the primary aci-nitro intermediates.
Published in:
- Journal of the American Chemical Society. - 2005
English
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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closed
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https://folia.unifr.ch/global/documents/224341
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