Photoinduced Skeletal Rearrangement of Diarylethenes: Photorelease of Lewis Acid and Synthetic Applications Full article
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Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263 |
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| Output data | Year: 2021, Volume: 86, Number: 23, Pages: 16806-16814 Pages count : 9 DOI: 10.1021/acs.joc.1c02033 | ||||
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Abstract:
The skeletal photorearrangement including 6π-electrocyclization induced by UV light of ortho-halogen-substituted diarylethenes has been studied. It has been found that the reaction pathways leading to bi- or tricyclic frameworks depend on the kind of halogen substituent and solvent. Photocyclization with halogen abstraction leads to bicyclic fused aromatics, while the tricyclic frameworks are formed due to the tandem 6π-electrocyclization/sigmatropic shift reaction. THF is preferred as the solvent in the former process and chloroform in the latter reaction. It was found for the first time that, owing to the ability of this series of diarylethenes to undergo skeletal photorearrangement with the release of the bromide cation, they can be used both as brominating agents and as Lewis acids for catalyzing electrophilic reactions.
Cite:
Zakharov A.V.
, Yadykov A.V.
, Gaeva E.B.
, Metelitsa A.V.
, Shirinian V.Z.
Photoinduced Skeletal Rearrangement of Diarylethenes: Photorelease of Lewis Acid and Synthetic Applications
Journal of Organic Chemistry. 2021. V.86. N23. P.16806-16814. DOI: 10.1021/acs.joc.1c02033 WOS Scopus OpenAlex
Photoinduced Skeletal Rearrangement of Diarylethenes: Photorelease of Lewis Acid and Synthetic Applications
Journal of Organic Chemistry. 2021. V.86. N23. P.16806-16814. DOI: 10.1021/acs.joc.1c02033 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000752848600049 |
| Scopus: | 2-s2.0-85118885893 |
| OpenAlex: | W3210355264 |