Реферат: A skeletal photorearrangement involving UV-induced 6π-electrocyclization of diarylethenes with various ethene bridges has been studied. It has been found that deprotonation is the predominant step among the three possible alternative reaction pathways (radical abstraction, deprotonation, or sigmatropic shift) following 6π-electrocyclization, and incorporation of an electronegative carbonyl group into the geminal position to the phenyl residue results in a reduction in the reaction time and an increase in the yield of the desired product. The significant increase in the reaction time in less polar solvents (toluene, TCM) also indicates a large contribution of the deprotonation step to the skeletal photorearrangement of diarylethenes. Performing the reaction in toluene in the presence of tertiary amines leads to a reduction in the reaction time and an increase in the yield of the desired product. The best results were achieved when the reaction was carried out in toluene in the presence of DIPEA. The experimental results are in good agreement with the DFT calculations.

Библиографическая ссылка: Shirinian V.Z. , Zakharov A.V. , Timofeeva S.M. , Yadykov A.V. , Krayushkin M.M.
Skeletal photoinduced rearrangement of diarylethenes: ethene bridge effects
Organic & Biomolecular Chemistry. 2023. V.21. N9. P.2015-2023. DOI: 10.1039/d2ob02315f WOS Scopus OpenAlex

Идентификаторы БД:

Web of science:	WOS:000930565500001
Scopus:	2-s2.0-85148751716
OpenAlex:	W4319751536

Цитирование в БД:

БД	Цитирований
OpenAlex	2
Scopus	3
Web of science	15

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