Photochemistry of S-Phenacyl Xanthates
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F11%3A00050098" target="_blank" >RIV/00216224:14310/11:00050098 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1021/jo201385b" target="_blank" >http://dx.doi.org/10.1021/jo201385b</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/jo201385b" target="_blank" >10.1021/jo201385b</a>
Alternative languages
Result language
angličtina
Original language name
Photochemistry of S-Phenacyl Xanthates
Original language description
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 compoundis 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 thexanthate moiety represents a photolabile linker. The photochemically released phenacyl radical fragments efficiently but reversibly add to the thiocarbonyl group of the parent xanthate molecule.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2011
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
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Volume of the periodical
76
Issue of the periodical within the volume
20
Country of publishing house
US - UNITED STATES
Number of pages
11
Pages from-to
8232-8242
UT code for WoS article
000295816700010
EID of the result in the Scopus database
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