C–Me Bond Formation at All Methylene Bridges of the Calix[4]arene Scaffold

A reaction of a distal dibromo diketocalix[4]­arene with excess MeLi, followed by acid-catalyzed dehydration, yields a derivative with a pair of opposite exocyclic double bonds, and a pair of trans methyl groups at the bridges. A reaction of a tetrabromo calix[4]­arene derivative with excess MeLi yi...

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Veröffentlicht in:Organic letters 2018-06, Vol.20 (11), p.3390-3393
Hauptverfasser: Shalev, Ori, Biali, Silvio E
Format: Artikel
Sprache:eng
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Zusammenfassung:A reaction of a distal dibromo diketocalix[4]­arene with excess MeLi, followed by acid-catalyzed dehydration, yields a derivative with a pair of opposite exocyclic double bonds, and a pair of trans methyl groups at the bridges. A reaction of a tetrabromo calix[4]­arene derivative with excess MeLi yields a calix[4]­arene derivative with all methylene bridges monomethylated in all-cis fashion.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01314