Monosodium salt of p-tert-butylcalix[4]arene in the reactions with electrophilic reagents. Synthesis and structure of monofunctionalized calix[4]arenes

Monosodium salt of p - tert -butylcalix[4]arene reacts with alkyl halides or aroyl chlorides in DMF formed the cone -shaped monoalkyloxycalix[4]arenes or 1,3-diacyloxycalix[4]arenes, respectively. Diacyloxycalix[4]arenes are easily transformed into monoacyloxycalix[4]arenes in the partial cone confo...

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Published inJournal of Inclusion Phenomena and Macrocyclic Chemistry Vol. 74; no. 1-4; pp. 265 - 275
Main Authors Yesypenko, Olexander A., Boyko, Vyacheslav I., Klyachina, Mariia A., Shishkina, Svitlana V., Shishkin, Oleg V., Pyrozhenko, Volodymyr V., Tsymbal, Ivan F., Kalchenko, Vitaly I.
Format Journal Article
LanguageEnglish
Published Dordrecht Springer Netherlands 01.12.2012
Subjects
Chemistry
Chemistry and Materials Science
Crystallography and Scattering Methods
Food Science
Organic Chemistry
Original Article
Conformers
butylcalixarenes
1,3-diacyloxy
Monoalkyloxy
Monoacyloxy
Alkylation
Acylation
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Summary:Monosodium salt of p - tert -butylcalix[4]arene reacts with alkyl halides or aroyl chlorides in DMF formed the cone -shaped monoalkyloxycalix[4]arenes or 1,3-diacyloxycalix[4]arenes, respectively. Diacyloxycalix[4]arenes are easily transformed into monoacyloxycalix[4]arenes in the partial cone conformation by interaction with NaOMe. The influence of intramolecular hydrogen bonding on course of alkylation and acylation reactions as well as the structure of the synthesized compounds in solution and crystalline state are discussed. Graphical Abstract  
ISSN:0923-0750
1573-1111
DOI:10.1007/s10847-012-0109-9