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@article{747255, author = {Literák, Jaromír and Hroudná, Ľubica and Klán, Petr}, article_location = {Amsterdam, The Netherlands}, article_number = {1}, keywords = {Photochemistry; Hydrogen abstraction; Electron transfer; Indanone; Indandione; Carboxylic acid esters}, language = {eng}, issn = {1010-6030}, journal = {Journal of Photochemistry and Photobiology A: Chemistry}, title = {1-Oxoindan-2-yl and 1,3-dioxoindan-2-yl esters as photoremovable protecting groups}, volume = {194}, year = {2008} }
TY - JOUR ID - 747255 AU - Literák, Jaromír - Hroudná, Ľubica - Klán, Petr PY - 2008 TI - 1-Oxoindan-2-yl and 1,3-dioxoindan-2-yl esters as photoremovable protecting groups JF - Journal of Photochemistry and Photobiology A: Chemistry VL - 194 IS - 1 SP - 59-66 EP - 59-66 PB - Elsevier Science SN - 10106030 KW - Photochemistry KW - Hydrogen abstraction KW - Electron transfer KW - Indanone KW - Indandione KW - Carboxylic acid esters N2 - 1-Oxoindan-2-yl and 1,3-dioxoindan-2-yl carboxylic acid esters react with an excess of H atom or e donors to release the corresponding acids, in addition to indan-1-one and indan-1,3-dione, respectively, as by-products. The maximum degradation quantum yields of 1-oxoindan-2-yl esters in propan-2-ol were found to approach 10, indicating that a chain reaction process, involving hydrogen transfer from the ketyl radical intermediates formed from an excited ester by hydrogen abstraction from an alcohol, participates. Such a cleavage mechanism parallels that observed earlier in photolysis of phenacyl esters. The corresponding 4,7-dimethyl substituted derivatives showed no contribution of the photoenolization mechanism apparently because of electronic and geometric reasons. Both 1-oxoindan-2-yl and 1,3-dioxoindan-2-yl chromophores are proposed to be utilized as photoremovable protecting groups in applications when higher concentrations of the hydrogen/electron donors are feasible. ER -
LITERÁK, Jaromír, Ľubica HROUDNÁ a Petr KLÁN. 1-Oxoindan-2-yl and 1,3-dioxoindan-2-yl esters as photoremovable protecting groups. \textit{Journal of Photochemistry and Photobiology A: Chemistry}. Amsterdam, The Netherlands: Elsevier Science, 2008, roč.~194, č.~1, s.~59-66. ISSN~1010-6030.
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