Unusual reactivity of upper-rim bridged calix[4]arenes - Friedel-Crafts alkylation via cleavage of the macrocyclic skeleton

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F18%3A43916446" target="_blank" >RIV/60461373:22310/18:43916446 - isvavai.cz</a>

Result on the web

<a href="https://www.sciencedirect.com/science/article/pii/S0040403918303988?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0040403918303988?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tetlet.2018.03.072" target="_blank" >10.1016/j.tetlet.2018.03.072</a>

Result language

angličtina

Original language name

Unusual reactivity of upper-rim bridged calix[4]arenes - Friedel-Crafts alkylation via cleavage of the macrocyclic skeleton

Original language description

Upper-rim bridged derivatives of calix[4]arenes, prepared by direct introduction of mercury into the meta position of basic skeleton followed by Pd-catalyzed intramolecular bridging, represent a novel type of calixarenes bearing an additional single bond between the meta positions of neighboring aromatic units. Due to the presence of a short bridge, these compounds exhibit extremely distorted cavities if compared with common calix[4]arenes. As a consequence of highly enhanced inner strain, the bridged compounds can be cleaved under acidic conditions to form open oligomeric species (carbocation of benzylic type) that can be used for the Friedel–Crafts alkylation of the aromatic compounds. This behavior, never observed in classic calix[4]arenes, documents conclusively a reasonably amended reactivity invoked by the additional bridge.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

<a href="/en/project/GA16-13869S" target="_blank" >GA16-13869S: Intramolecularly bridged calixarenes as new building blocks in supramolecular chemistry</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

Name of the periodical

Tetrahedron Letters

ISSN

0040-4039

e-ISSN

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Volume of the periodical

59

Issue of the periodical within the volume

18

Country of publishing house

GB - UNITED KINGDOM

Number of pages

3

Pages from-to

1757-1759

UT code for WoS article

000430778700016

EID of the result in the Scopus database

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