CuAAC and RuAAC with Alkyne-functionalised Dihydroazulene Photoswitches and Determination of Hammett σ-Constants for Triazoles

Content Provider	Semantic Scholar
Author	Lissau, Henriette Broman, Søren Lindbæk Jevric, Martyn Madsen, Anders Ø. Nielsen, Mogens Brøndsted
Copyright Year	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.
Starting Page	531
Ending Page	534
Page Count	4
File Format	PDF HTM / HTML
DOI	10.1071/CH13544
Volume Number	67
Alternate Webpage(s)	http://www.publish.csiro.au/ch/acc/CH13544/CH13544_AC.pdf
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article