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Updated: May 21, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Synthesis and resolution of a 1,1'-biazulene analogue of BINOL
Anthony P Gee1, Tiberiu-M Gianga1, Gabriele Kociok-Köhn2
1Department of Chemistry, University of Bath Bath BA2 7AY UK S.E.Lewis@bath.ac.uk.
Abstract:
Biaryls exhibiting axial chirality have been extensively exploited in fields such as asymmetric catalysis, but the biaryl linkage typically consists of benzenoid aromatic rings, with non-benzenoid biaryls being scarce. Here we report the first preparation of a (non-benzenoid) 1,1'-biazulene-2,2'-diol ("1,1'-BAzOL") in enantiopure form and determine its barrier to racemisation. Furthermore we transformed a 1,1'-biazulene-2,2'-diol into the corresponding 2,2'-bis(phosphonate), thereby demonstrating functional group interconversion through cross coupling and highlighting the potential for diversification.
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