Comparison of Photocyclization Reactions of Fluoro- vs Nonfluoro-Substituted Polymethyleneoxy Donor Linked Phthalimides

Title
Comparison of Photocyclization Reactions of Fluoro- vs Nonfluoro-Substituted Polymethyleneoxy Donor Linked Phthalimides
Author(s)
조대원박혜정[박혜정]류영주[류영주]김경목[김경목]윤웅찬[윤웅찬]김은애[김은애]손영구Patrick S. Mariano[Patrick S. Mariano]
Keywords
SELECTIVE ELECTROCHEMICAL OXIDATION; ASSISTED SEQUENTIAL INTRODUCTION; CARBON BOND FORMATION; CROWN-ETHERS; ORGANOSILICON COMPOUNDS; HETEROATOM COMPOUNDS; N-ALKYLPHTHALIMIDES; SET PHOTOCHEMISTRY; ORGANOTHIO GROUPS; ANODIC-OXIDATION
Issue Date
201304
Publisher
KOREAN CHEMICAL SOC
Citation
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.34, no.4, pp.1108 - 1114
Abstract
Photochemical reactions of fluoro- vs. nonfluoro-substituted polymethylenoxy chain linked phthalimide were carried out to explore how electronegative fluorine atoms inside the donor chain influence photocyclization reaction efficiencies and to briefly determine the alkali metal binding properties of the photoproducts. The results of this study show that the fluorine-substituted donor chain linked phthalimide undergoes inefficient photocyclization via single electron transfer (SET)-induced excited state pathways to generate 14-membered cyclic amidol compared to nonfluoro-analog due to low electron donor ability of the terminal oxygen donor site. These results show that photoinduced intramolecular SET processes arising from alpha-silyl ether electron donors to phthalimides are largely dependent on the kinds of substituents inside donor chain. Finally, a preliminary study with the cyclic amidols generated in this effort showed that they have weak alkali metal cation binding properties regardless of absence/presence of fluoro-substituents.
URI
http://hdl.handle.net/YU.REPOSITORY/26063http://dx.doi.org/10.5012/bkcs.2013.34.4.1108
ISSN
0253-2964
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이과대학 > 화학생화학부 > Articles
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