TAZHE VEETIL, Aneesh, Tomáš ŠOLOMEK, Bokolombe Pitchou NGOY, Nela PAVLÍKOVÁ, Dominik HEGER a Petr KLÁN. Photochemistry of S-Phenacyl Xanthates. Journal of Organic Chemistry. Columbus, OH, USA: the American Chemical Society, 2011, roč. 76, č. 20, s. 8232-8242. ISSN 0022-3263. Dostupné z: https://dx.doi.org/10.1021/jo201385b. |
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@article{955976, author = {Tazhe Veetil, Aneesh and Šolomek, Tomáš and Ngoy, Bokolombe Pitchou and Pavlíková, Nela and Heger, Dominik and Klán, Petr}, article_location = {Columbus, OH, USA}, article_number = {20}, doi = {http://dx.doi.org/10.1021/jo201385b}, keywords = {Reversible addition-fragmentation transfer; RAFT; macromolecular design via the interchange of xanthates; MADIX; xanthates; phenacyl compounds; photochemistry; photoremovable protecting groups; laser flash spectroscopy; DFT calculations.}, language = {eng}, issn = {0022-3263}, journal = {Journal of Organic Chemistry}, title = {Photochemistry of S-Phenacyl Xanthates}, volume = {76}, year = {2011} }
TY - JOUR ID - 955976 AU - Tazhe Veetil, Aneesh - Šolomek, Tomáš - Ngoy, Bokolombe Pitchou - Pavlíková, Nela - Heger, Dominik - Klán, Petr PY - 2011 TI - Photochemistry of S-Phenacyl Xanthates JF - Journal of Organic Chemistry VL - 76 IS - 20 SP - 8232-8242 EP - 8232-8242 PB - the American Chemical Society SN - 00223263 KW - Reversible addition-fragmentation transfer KW - RAFT KW - macromolecular design via the interchange of xanthates KW - MADIX KW - xanthates KW - phenacyl compounds KW - photochemistry KW - photoremovable protecting groups KW - laser flash spectroscopy KW - DFT calculations. N2 - Various synthetically readily accessible S-phenacyl xanthates are shown to undergo photoinitiated homolytic scission of the C-S bond in the primary step. The resultant fragments, phenacyl and xanthic acid radicals, recombine to form symmetrical 1,4-diketones and xanthogen disulfides, respectively, in high to moderate chemical yields in chemically inert solvents. They can also be efficiently trapped by a hydrogen-atom donating solvent to give acetophenone and xanthic acid derivatives. The latter compound is in situ thermally converted to the corresponding alcohol in high chemical yields. S-Phenacyl xanthates could thus be utilized as synthetic precursors to the above mentioned compounds, or as photoremovable protecting groups for alcohols, in which the xanthate moiety represents a photolabile linker. The photochemically released phenacyl radical fragments efficiently but reversibly add to the thiocarbonyl group of the parent xanthate molecule. ER -
TAZHE VEETIL, Aneesh, Tomáš ŠOLOMEK, Bokolombe Pitchou NGOY, Nela PAVLÍKOVÁ, Dominik HEGER a Petr KLÁN. Photochemistry of S-Phenacyl Xanthates. \textit{Journal of Organic Chemistry}. Columbus, OH, USA: the American Chemical Society, 2011, roč.~76, č.~20, s.~8232-8242. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/jo201385b.
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