TY - JOUR
T1 - CuAAC and RuAAC with alkyne-functionalised Dihydroazulene photoswitches and determination of Hammett σ-constants for Triazoles
AU - Lissau, Henriette Schjøtt
AU - Broman, Søren Lindbæk
AU - Jevric, Martyn
AU - Madsen, Anders Østergaard
AU - Nielsen, Mogens Brøndsted
PY - 2014
Y1 - 2014
N2 - Dihydroazulene (DHA)-vinylheptafulvene (VHF) photoswitches have attracted attention as potentially useful components in molecular electronics. The p-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.
AB - Dihydroazulene (DHA)-vinylheptafulvene (VHF) photoswitches have attracted attention as potentially useful components in molecular electronics. The p-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.
U2 - 10.1071/ch13544
DO - 10.1071/ch13544
M3 - Journal article
SN - 0004-9425
VL - 67
SP - 531
EP - 534
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
IS - 3
ER -