Photocyclization of Diarylethenes: The Effect of Electron and Proton Acceptors as Additives

Photocyclization of Diarylethenes: The Effect of Electron and Proton Acceptors as Additives Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2021, Volume: 86, Number: 15, Pages: 10023-10031 Pages count : 9 DOI: 10.1021/acs.joc.1c00723

Authors

Yadykov Anton V. ¹ , Lvov Andrey G. ² , Krayushkin Mikhail M. ¹ , Zakharov Alexey V. ¹ , Shirinian Valerii Z. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky Prospect, Moscow 119991, Russian Federation
2	Irkutsk National Research Technical University, 83, Lermontov Street, Irkutsk 664074, Russian Federation

The effect of electron and proton acceptors on the photocyclization of diarylethenes has been studied. Without any additives, the deprotonation reaction is predominant, although other processes, including the sigmatropic shift, are not excluded. A deuterium exchange experiment has shown that a strong base (DABCO) facilitates the deprotonation reaction, thereby limiting the sigmatropic shift. In the presence of an oxidizing agent or additional sources of radicals (O2, I2, TEMPO), the processes of deprotonation and rearrangement (H-shift) are practically not observed, and the reaction proceeds along a radical pathway with the formation of phenanthrene or its heterocyclic analogue.

Yadykov A.V. , Lvov A.G. , Krayushkin M.M. , Zakharov A.V. , Shirinian V.Z.
Photocyclization of Diarylethenes: The Effect of Electron and Proton Acceptors as Additives
Journal of Organic Chemistry. 2021. V.86. N15. P.10023-10031. DOI: 10.1021/acs.joc.1c00723 WOS Scopus OpenAlex

Web of science:	WOS:000684025500009
Scopus:	2-s2.0-85112686336
OpenAlex:	W3184517330

DB	Citing
OpenAlex	21
Scopus	21
Web of science	18