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1-Oxoindan-2-yl and 1,3-dioxoindan-2-yl esters as photoremovable protecting groups

Paper ID Volume ID Publish Year Pages File Format Full-Text
28823 44094 2008 8 PDF Available
Title
1-Oxoindan-2-yl and 1,3-dioxoindan-2-yl esters as photoremovable protecting groups
Abstract

1-Oxoindan-2-yl and 1,3-dioxoindan-2-yl carboxylic acid esters react with an excess of hydrogen atom or electron 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 H-donating 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 experimentally feasible.

Keywords
Photochemistry; Hydrogen abstraction; Electron transfer; Indanone; Indandione; Carboxylic acid esters
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1-Oxoindan-2-yl and 1,3-dioxoindan-2-yl esters as photoremovable protecting groups
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 194, Issue 1, 5 February 2008, Pages 59–66
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us