Synthetic Route to Phenyl Diazenes and Pyridazinium Salts from Phenylazosulfonates.
J Org Chem
; 86(9): 6228-6238, 2021 May 07.
Article
em En
| MEDLINE
| ID: mdl-33900767
ABSTRACT
The synthesis of pyridazinium salts was achieved from readily available phenylazosulfonates in a single reaction step. The reaction proceeds via the formation of short-lived phenyldiazenes, which-owing to the strongly acidic conditions-are partially protonated. The phenyldiazenes then undergo a rapid cycloaddition to furans to give pyridazinium salts via elimination of water. The fact that the pyridazinium synthesis shows a low sensitivity toward oxygen, although phenyldiazenes occur as intermediates, can be explained by the very fast cycloaddition step and the partial protonation of the phenyldiazene.
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MEDLINE
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En
Ano de publicação:
2021
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Article