4,5,12,13-Tetrabromo[2.2]paracyclophane - A New Bis(aryne) Equivalent - University of Regensburg Publication Server

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

Preview

PDF
(417kB)

Date of publication of this fulltext: 05 Aug 2009 13:51

Alternative links to fulltext:

Details

Preview

Export bibliographical data

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. ...