Multispin Systems with a Rigid Ferrocene‐1,1′‐diyl‐Substituted 1,3‐Diazetidine‐2,4‐diimine Coupler: A General Approach

Multispin Systems with a Rigid Ferrocene‐1,1′‐diyl‐Substituted 1,3‐Diazetidine‐2,4‐diimine Coupler: A General Approach Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2022, Volume: 2022, Number: 7, Article number : e202101234, Pages count : DOI: 10.1002/ejoc.202101234

Authors

Gurskaya Larisa Yu. ¹ , Polienko Yuliya F. ¹ , Rybalova Tatyana V. ¹ , Gritsan Nina P. ² , Dmitriev Alexey A. ² , Kazantsev Maxim S. ¹ , Zaytseva Elena V. ¹ , Parkhomenko Dmitry A. ¹ , Beregovaya Irina V. ¹ , Zakabluk Galina A. ³ , Tretyakov Evgeny V. ⁴

Affiliations

1	N. N. Vorozhtsov Institute of Organic Chemistry Siberian Branch (SB) of Russian Academy of Sciences (RAS), 9 Ac. Lavrentiev Avenue, Novosibirsk 630090, Russia
2	V. V. Voevodsky Institute of Chemical Kinetics and Combustion, SB RAS, 3 Institutskaya Str., Novosibirsk 630090, Russia
3	Institute of Chemical Biology and Fundamental Medicine, SB RAS, 8 Ac. Lavrentiev Avenue, Novosibirsk 630090, Russia
4	N. D. Zelinsky Institute of Organic Chemistry, RAS 47 Leninsky Avenue, Moscow 119991, Russia

This paper describes the stepwise aza-Wittig reaction of 1,1′-bis(triphenylphosphoranylidenamino)-ferrocene with a paramagnetic isocyanate, namely, 3-isocyanato-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-1-oxyl, and then with substituted arylisocyanates. The intermediate product (a paramagnetic betaine), which is the product of an intramolecular nucleophilic attack of the nitrogen atom of the iminophosphorane moiety on the carbon atom of the carbodiimide functional group, was isolated and structurally characterized. Subsequent interaction of the betaine with arylisocyanates under mild conditions gave spin-labeled ferrocenophanes with the 1,3-diazetidine-2,4-diimine coupler. It was found that the mutual arrangement of the substituents in the latter depends on the nature of the substituents in the arylisocyanate. Iodophenyl derivatives of 1,3-diazetidine-2,4-diimines were cross-coupled with the gold(I) nitronyl nitroxide-2-ide complex, thus yielding diradicals: metallocenophanes functionalized with various types of nitroxide substituents. Molecular and crystal structures of all mono- and diradicals were solved by X-ray diffraction analysis.

Gurskaya L.Y. , Polienko Y.F. , Rybalova T.V. , Gritsan N.P. , Dmitriev A.A. , Kazantsev M.S. , Zaytseva E.V. , Parkhomenko D.A. , Beregovaya I.V. , Zakabluk G.A. , Tretyakov E.V.
Multispin Systems with a Rigid Ferrocene‐1,1′‐diyl‐Substituted 1,3‐Diazetidine‐2,4‐diimine Coupler: A General Approach
European Journal of Organic Chemistry. 2022. V.2022. N7. e202101234 . DOI: 10.1002/ejoc.202101234 WOS Scopus OpenAlex

Web of science:	WOS:000743567600001
Scopus:	2-s2.0-85122854758
OpenAlex:	W4200444859

DB	Citing
OpenAlex	5
Scopus	4