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3v symmetrical calixarene core is symbolized by H and the small and large rim substituents are depicted by exponents and indexes, respectively.
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1H NMR spectra of the crude chlorosulfonyl-calixarenes isolated by precipitation with ether, these reactive intermediates were relatively pure and a unique regio-isomer was identified. Further purification for elemental analyses purpose failed, probably due to partial and uncontrolled hydrolysis or polymerisation when dried under high vacuum. Therefore, they were directly engaged in either hydrolysis or aminolysis.
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14
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note
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O-Protection of diethanolamine by tertiobutyldimethylsilyl groups (TBDMS) appeared necessary to avoid competitive hydrolysis of the chlorosulfonyl intermediate. Indeed, when unprotected diethanolamine was used, sulfonate derivatives were obtained.
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