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41.7.2.1.4.3 Variation 3: From Alk-1-enyltriazenes

DOI: 10.1055/sos-SD-041-00494

Kubik, S.Science of Synthesis, (201041528.

The acid-induced decomposition of alkyl(aryl)triazenes is a general method for the generation of alkanediazonium compounds (see Section 41.7.1.1.2) which can also be used to prepare alkenediazonium compounds by starting from alk-1-enyl(aryl)triazene derivatives. The reaction conditions usually do not allow isolation of the alkenediazonium compound, which acts only as a short-lived intermediate. The example depicted in Scheme 35 shows that the major product derives from reaction of the acid used to induce triazene decomposition with the rearranged vinyl cation that is formed from the alkenediazonium ion.[‌141‌]

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