Synthesis and Reactivity of 1‑Allenyltriazenes
datasetposted on 31.03.2017, 12:03 by Loïc N. Jeanbourquin, Rosario Scopelliti, Farzaneh Fadaei Tirani, Kay Severin
1-Aryl-3,3-dialkyltriazenes have received considerable attention in the context of synthetic and medicinal chemistry. In contrast, the chemistry of other unsaturated triazenes is largely unexplored. The synthesis of 1‑allenyltriazenes is described. This new class of compounds can be obtained by base-induced isomerization of 1‑alkynyltriazenes. The latter are accessible by reaction of alkynyl Grignard reagents with lithium amides and nitrous oxide. 1-Allenyltriazenes were found to be thermally labile, but they can be stored without degradation at lower temperatures. In the presence of ZnCl2, 1-allenyltriazenes rearrange into N‑aminopyrazoles.