title: 1-Alkynyltriazenes as Functional Analogues of Ynamides.
abstract: The chemical reactivity of 1-alkynyltriazenes has been investigated and is found to parallel the reactivity of ynamides. The similarity in reactivity of these two classes of compounds is demonstrated by addition reactions with acids, by cycloaddition reactions with ketenes, tetracyanoethene, and cyclopropanes, as well as by intramolecular cyclization reactions. The presence of reactive triazene groups in the products enables subsequent transformations. Overall, our results suggest that 1-alkynyltriazenes should become valuable reagents in synthetic organic chemistry.
authors.affiliation: Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, (Switzerland).
authors.forename: Florian G
authors.initials: FG
authors.lastname: Perrin
authors.affiliation: Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, (Switzerland).
authors.forename: Gregor
authors.initials: G
authors.lastname: Kiefer
authors.affiliation: Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, (Switzerland).
authors.forename: Loïc
authors.initials: L
authors.lastname: Jeanbourquin
authors.affiliation: Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, (Switzerland).
authors.forename: Sophie
authors.initials: S
authors.lastname: Racine
authors.affiliation: Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, (Switzerland).
authors.forename: Daniele
authors.initials: D
authors.lastname: Perrotta
authors.affiliation: Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, (Switzerland).
authors.forename: Jérôme
authors.initials: J
authors.lastname: Waser
authors.affiliation: Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, (Switzerland).
authors.forename: Rosario
authors.initials: R
authors.lastname: Scopelliti
authors.affiliation: Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, (Switzerland). kay.severin@epfl.ch.
authors.forename: Kay
authors.initials: K
authors.lastname: Severin
keywords: alkynes; cyclization; cycloaddition reactions; triazenes; ynamides