| TAZHE VEETIL, Aneesh, Tomáš ŠOLOMEK, Bokolombe Pitchou NGOY, Nela PAVLÍKOVÁ, Dominik HEGER and Petr KLÁN. Photochemistry of S-Phenacyl Xanthates. Journal of Organic Chemistry. Columbus, OH, USA: the American Chemical Society, 2011, vol. 76, No 20, p. 8232-8242. ISSN 0022-3263. Available from: 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 and Petr KLÁN. Photochemistry of S-Phenacyl Xanthates. \textit{Journal of Organic Chemistry}. Columbus, OH, USA: the American Chemical Society, 2011, vol.~76, No~20, p.~8232-8242. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/jo201385b.
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