Unlocking Kuhn Verdazyls: New Synthetic Approach and Useful Mechanistic Insights Full article
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International Journal of Molecular Sciences
ISSN: 1661-6596 , E-ISSN: 1422-0067 |
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| Output data | Year: 2023, Volume: 24, Number: 3, Article number : 2693, Pages count : DOI: 10.3390/ijms24032693 | ||
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Abstract:
An optimized synthetic protocol toward the assembly of Kuhn verdazyls based on an azo coupling of arenediazonium salts with readily available hydrazones followed by the base-mediated cyclization of in situ formed formazans with formalin was developed. The scope and limitations of the presented method were revealed. Some new mechanistic insights on the formation of Kuhn verdazyls were also conducted. It was found that in contradiction with previously assumed hypotheses, the synthesis of verdazyls was accomplished via an intermediate formation of verdazylium cations which were in situ reduced to leucoverdazyls. The latter underwent deprotonation under basic conditions to generate corresponding anions which coproportionate with verdazylium cations to furnish the formation of Kuhn verdazyls. The spectroscopic and electrochemical behavior of the synthesized verdazyls was also studied. Overall, our results may serve as a reliable basis for further investigation in the chemistry and applications of verdazyls.
Cite:
Teslenko F.E.
, Fershtat L.L.
Unlocking Kuhn Verdazyls: New Synthetic Approach and Useful Mechanistic Insights
International Journal of Molecular Sciences. 2023. V.24. N3. 2693 . DOI: 10.3390/ijms24032693 WOS Scopus OpenAlex
Unlocking Kuhn Verdazyls: New Synthetic Approach and Useful Mechanistic Insights
International Journal of Molecular Sciences. 2023. V.24. N3. 2693 . DOI: 10.3390/ijms24032693 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000930796300001 |
| Scopus: | 2-s2.0-85147895509 |
| OpenAlex: | W4318828654 |