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Synthesis and Reactivity of 1‑Allenyltriazenes

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posted on 31.03.2017, 12:04 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.