CuAAC and RuAAC with Alkyne-functionalised Dihydroazulene Photoswitches and Determination of Hammett σ-Constants for Triazoles
Henriette Lissau A , Søren Lindbæk Broman A , Martyn Jevric A , Anders Ø. Madsen A and Mogens Brøndsted Nielsen A B
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark.
B Corresponding author. Email: mbn@kiku.dk
Australian Journal of Chemistry 67(3) 531-534 https://doi.org/10.1071/CH13544
Submitted: 9 October 2013 Accepted: 21 November 2013 Published: 6 January 2014
Abstract
Dihydroazulene (DHA)–vinylheptafulvene (VHF) photoswitches have attracted attention as potentially useful components in molecular electronics. The π-conjugated dihydroazulene system is a rigid structure and can be strategically functionalised to place handles for further elaboration. Here we show that alkyne-functionalised dihydroazulenes can be subjected to copper and ruthenium catalysed azide–alkyne cycloadditions (CuAAC and RuAAC) with tolylazide, furnishing 1,4- and 1,5-disubstituted triazoles. The rates of ring-closure of the corresponding vinylheptafulvenes were compared with those of reference systems, which allowed determination of Hammett substituent constants (meta and para) for N-tolyl-substituted 1,2,3-triazoles.
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