S-Alkylation of Thiacalixarenes: How the Regio- and Stereoselectivities Depend on the Starting Conformation

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/60461373:22810/12:43894908

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

S-Alkylation of Thiacalixarenes: How the Regio- and Stereoselectivities Depend on the Starting Conformation

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

S-Alkylation of Thiacalixarenes: How the Regio- and Stereoselectivities Depend on the Starting Conformation

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2012

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

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Svazek periodika

77

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

2272-2278

Kód UT WoS článku

000300915900020

EID výsledku v databázi Scopus

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