Addition of cyanomethyl anion to the cyano group of 2-cyano-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl, a nitronyl nitroxide

Addition of cyanomethyl anion to the cyano group of 2-cyano-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl, a nitronyl nitroxide Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2016, Volume: 57, Number: 21, Pages: 2327-2330 Pages count : 4 DOI: 10.1016/j.tetlet.2016.04.070

Tags

Polyfunctional nitronyl nitroxides; Spin-labeled enaminonitrile; Cyanomethyl anion addition; Reactions in liquid ammonia

Authors

Tretyakov Evgeny V. ^1,2 , Peshkov Roman Yu. ^1,2 , Panteleeva Elena V. ^1,2 , Scrypnik Andrey S. ² , Stass Dmitri V. ^2,3 , Romanenko Galina V. ⁴ , Ovcharenko Victor I. ⁴

Affiliations

1	(Данные Web of science) NN Vorozhtsov Inst Organ Chem, 9 Ac Lavrentiev Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova Str, Novosibirsk 630090, Russia
3	(Данные Web of science) Inst Chem Kinet & Combust, 3 Inst Skaya Str, Novosibirsk 630090, Russia
4	(Данные Web of science) Int Tomog Ctr, 3a Inst Skaya Str, Novosibirsk 630090, Russia

Addition of the cyanomethyl anion to the triple bond of the cyano group in 2-cyano-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl with the formation of stable (Z)-3-amino-3-(4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl-2-yl)acrylonitrile is reported. The product yield was dependent on the cyanomethyl anion salt counter-ion and was highest in the case of the potassium salt in liquid ammonia. Crystallization provided at least two polymorphs of the synthesized nitroxide according to single crystal X-ray data. ESR spectroscopy revealed delocalization of unpaired electron spin density into the enaminonitrile substituent. The synthesized nitronyl nitroxide is of interest for the preparation of new polyfunctional nitroxides and as polydentate paramagnetic ligands. (C) 2016 Elsevier Ltd. All rights reserved.

Tretyakov E.V. , Peshkov R.Y. , Panteleeva E.V. , Scrypnik A.S. , Stass D.V. , Romanenko G.V. , Ovcharenko V.I.
Addition of cyanomethyl anion to the cyano group of 2-cyano-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl, a nitronyl nitroxide
Tetrahedron Letters. 2016. V.57. N21. P.2327-2330. DOI: 10.1016/j.tetlet.2016.04.070 WOS Scopus РИНЦ

Published print:

May 1, 2016

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