Journal
ORGANIC LETTERS
Volume 19, Issue 8, Pages 2070-2073Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00671
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Funding
- Swiss National Science Foundation
- Ecole Polytechnique Federale de Lausanne (EPFL)
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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.
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