Studies of Silyl-Transfer Photochemical Reactions of N-[(Trimethylsilyl)alkyl]saccharins

Title
Studies of Silyl-Transfer Photochemical Reactions of N-[(Trimethylsilyl)alkyl]saccharins
Author(s)
조대원오선화[오선화]김동욱[김동욱]박혜정[박혜정]Jin Ying Xue[Jin Ying Xue]윤웅찬[윤웅찬]Patrick S. Mariano[Patrick S. Mariano]
Keywords
POLYDONOR-SUBSTITUTED PHTHALIMIDES; YLIDE-FORMING PHOTOREACTIONS; PHOTOCYCLIZATION REACTIONS; PHOTOADDITION REACTIONS; PHOTOINDUCED REACTIONS; SET PHOTOCHEMISTRY; CATION RADICALS; CYCLIC IMIDES; DERIVATIVES; EFFICIENT
Issue Date
201009
Publisher
KOREAN CHEMICAL SOC
Citation
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.31, no.9, pp.2453 - 2458
Abstract
Photochemical studies of N-[(trimethylsilyl)allcyl]saccharins were carried out to investigate their photochemical behavior. Depending on the nature of the substrate and the solvent system employed, reactions of these substances can take place by either SET-promoted silyl migration from carbon to either the amide carbonyl or sulfonyl oxygen or by a N-S homolysis route. The results of the current studies show that an azomethine ylide, arising from a SET-promoted silyl migration pathway, is generated in photoreactions of N-[(trimethylsilyl)methyl]saccharin and this intermediate reacts to give various photoproducts depending on the conditions employed. In addition, irradiation of N-[(trimethylsily)ethyl]saccharin produces an excited state that reacts through two pathways, the relative importance is governed by solvent polarity and protic nature. Finally, photoirradiation of N-[(trimethylsilyl)propyl]saccharin in a highly polar solvent system comprised of 35% aqueous MeOH gives rise to formation of a tricyclic pyrrolizidine and saccharin that generated via competitive SET-promoted silyl transfer and gamma-hydrogen abstraction pathways.
URI
http://hdl.handle.net/YU.REPOSITORY/23702http://dx.doi.org/10.5012/bkcs.2010.31.9.2453
ISSN
0253-2964
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이과대학 > 화학생화학부 > Articles
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