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research article

Synthesis and Reactivity of 1-Allenyltriazenes

Jeanbourquin, Loïc Nicolas  
•
Scopelliti, Rosario  
•
Fadaei Tirani, Farzaneh  
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2017
Organic Letters

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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Type
research article
DOI
10.1021/acs.orglett.7b00671
Web of Science ID

WOS:000400123600034

Author(s)
Jeanbourquin, Loïc Nicolas  
Scopelliti, Rosario  
Fadaei Tirani, Farzaneh  
Severin, Kay  
Date Issued

2017

Published in
Organic Letters
Volume

19

Start page

2070

End page

2073

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCS  
Available on Infoscience
April 7, 2017
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/136428
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