Reactions of terminal polyynes with benzyl azide.
Terminal di-, tri-, tetra-, and pentaynes substituted with a variety of functional groups react with benzyl azide in the presence of CuSO(4)·5H(2)O and ascorbic acid to give derivatives of 4-ethynyl-, 4-butadiynyl-, 4-hexatriynyl-, and 4-octatetraynyl-1,2,3-triazoles in moderate to good yields. These reactions appear to proceed regioselectively, and functionalization occurs exclusively at the terminal alkyne moiety. As well, no evidence of multiple azide additions to the polyyne framework is observed. X-ray crystallographic analysis of nine derivatives is used to document the regioselectivity of the reaction as well as outline structural characteristics of the 1,2,3-triazole products.
Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Thanh
T
Luu
Boris J
BJ
Medos
Erin R
ER
Graham
Danielle M
DM
Vallee
Robert
R
McDonald
Michael J
MJ
Ferguson
Rik R
RR
Tykwinski