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4,5,12,13-Tetrabromo[2.2]paracyclophane - A New Bis(aryne) Equivalent

URN to cite this document:
urn:nbn:de:bvb:355-epub-61536
DOI to cite this document:
10.5283/epub.6153
König, Burkhard ; Knieriem, Burkhard ; Rauch, K. ; Meijere, Armin de
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Date of publication of this fulltext: 05 Aug 2009 13:51


Abstract

The reaction of 2 with nBuLi at -78°C generates aryne intermediates within the aromatic rings of [2.2]paracyclophane which are trapped in Diels-Alder reactions with dienes like furan, 1,9-diphenylisobenzofuran, or cyclopentadiene. Reductive deoxygenation with low-valent titanium reagents or TMSI converts the adducts of furan and isobenzofuran into anti-[2.2]paracyclophanes 4 and 5, respectively. ...

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