Uncommon Regioselectivity in the Thiacalix[4]arene Series: Gross Formylation of the Cone Conformer
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F10%3A00023602" target="_blank" >RIV/60461373:22310/10:00023602 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Alternative languages
Result language
angličtina
Original language name
Uncommon Regioselectivity in the Thiacalix[4]arene Series: Gross Formylation of the Cone Conformer
Original language description
Thiacalix[4]arene immobilized in the cone conformation undergoes a direct Gross formylation reaction (Cl2CH-O-CH3/SnCl4/CH2Cl2) to give the upper-rim formylated thiacalixarene. Albeit using excess of the formylation agent and various reaction temperatures, only one formyl group is introduced into the meta position of the thiacalixarene skeleton. The surprising regioselectivity indicates dramatically different reactivity of the thiacalix[4]arene system when compared with a classical calix[4]arene analogue, which yields exclusively para isomers. The introduction of functional groups into the meta position represents an exceptional substitution pattern in thiacalixarene chemistry, which imparts in interesting conformational behavior to these compounds. The systematic NMR study revealed that the pinched cone-pinched cone equilibrium is remarkably shifted toward one pinched cone structure depending on the substitution.
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
2010
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
75
Issue of the periodical within the volume
2
Country of publishing house
US - UNITED STATES
Number of pages
5
Pages from-to
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UT code for WoS article
000273400300015
EID of the result in the Scopus database
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