S-Alkylation of Thiacalixarenes: How the Regio- and Stereoselectivities Depend on the Starting Conformation
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F12%3A43894908" target="_blank" >RIV/60461373:22310/12:43894908 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22810/12:43894908
Result on the web
<a href="http://dx.doi.org/10.1021/jo202571h" target="_blank" >http://dx.doi.org/10.1021/jo202571h</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/jo202571h" target="_blank" >10.1021/jo202571h</a>
Alternative languages
Result language
angličtina
Original language name
S-Alkylation of Thiacalixarenes: How the Regio- and Stereoselectivities Depend on the Starting Conformation
Original language description
S-alkylation of all four thiacalix[4]arene conformations was accomplished using alkyl triflates. The corresponding sulfonium salts are formed in a highly regio- and stereoselective manner depending on the conformation used. Interestingly, only mono- or disubstituted sulfonium salts can be prepared. Although many regio- and stereoisomers are theoretically possible, only one dialkylated cone and 1,2-alternate derivatives were formed, while only a single isomer of monoalkylated partial cone and 1,3-alternate were isolated. The combination of experimental results with the quantum-chemical approach using the B3LYP/6-311G(d,p) method resulted in the elucidation of the rules governing the regio- and stereochemical outcomes of the alkylation reactions. All S-alkylated compounds represent a novel type of substitution pattern in calixarene chemistry showing the wide-ranging possibility of thiacalixarene skeleton modifications.
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)
Others
Publication year
2012
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
77
Issue of the periodical within the volume
5
Country of publishing house
US - UNITED STATES
Number of pages
7
Pages from-to
2272-2278
UT code for WoS article
000300915900020
EID of the result in the Scopus database
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