An Improved Method for the Regiospecific Synthesis of Polysubstituted [2.2]Paracyclophanes

An Improved Method for the Regiospecific Synthesis of Polysubstituted [2.2]Paracyclophanes

Abstract 4,16-Disubstituted, 4,7,12,15-tetrasubstituted, 4,8,12,16-tetrasubstituted and 4,5,7,8,12,13,15,16-octasubstituted [2.2]paracyclophanes can be prepared in significantly improved yields and excellent regiospecificities via the Winberg 1,6-elimination-dimerization reaction from substituted (4...

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Veröffentlicht in:Synlett 2005-09, Vol.2005 (14), p.2130-2134
Hauptverfasser: Chow, Hak-Fun, Low, Kam-Hung, Wong, King Y.
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract 4,16-Disubstituted, 4,7,12,15-tetrasubstituted, 4,8,12,16-tetrasubstituted and 4,5,7,8,12,13,15,16-octasubstituted [2.2]paracyclophanes can be prepared in significantly improved yields and excellent regiospecificities via the Winberg 1,6-elimination-dimerization reaction from substituted (4-methylbenzyl)tri­methylammonium hydroxides. Using 2-chloro-phenothiazine instead of phenothiazine as a polymerization inhibitor results in a doubling of product yields.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2005-872270