Transalkylation of alkyl aryl sulfides with alkylating agents

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F18%3A10382760" target="_blank" >RIV/00216208:11160/18:10382760 - isvavai.cz</a>
Result on the web
<a href="http://www.sciencedirect.com/science/article/pii/S0040402017313133" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0040402017313133</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tet.2017.12.039" target="_blank" >10.1016/j.tet.2017.12.039</a>

Result language
angličtina
Original language name
Transalkylation of alkyl aryl sulfides with alkylating agents
Original language description
The reaction of methyl iodide with tert-butylphenylsulfide in DMF leads to a transalkylation that produces methylphenylsulfide. This transalkylation reaction was further studied by H-1 NMR spectroscopy. The polarity of the solvent, the electron density on the sulfur atom, and the strength of the alkylating agent (MeI, EtI, BuI, dimethyl sulfate, or dimethyl carbonate) played important roles in the reaction. The suggested mechanism of the reaction involves the formation of a dialkyl aryl sulfonium salt that subsequently eliminates the radical. This mechanism was supported by the observation of higher conversion rates for compounds with more branched alkyl groups on the sulfur atom, which may lead to the formation of more stable radicals.
Czech name
—
Czech description
—

Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GA17-19094S" target="_blank" >GA17-19094S: Azaphthalocyanines – dark quenchers in DNA hybridization probes</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Similar results(10)