Synthesis of Cyclic Vicinal Trifluoromethylated Hydroxylamine and Nitrone Based on Perfluorodiacetyl

Synthesis of Cyclic Vicinal Trifluoromethylated Hydroxylamine and Nitrone Based on Perfluorodiacetyl Full article

Journal

Journal of Heterocyclic Chemistry
ISSN: 0022-152X

Output data

Year: 2017, Volume: 54, Number: 3, Pages: 1887-1890 Pages count : 4 DOI: 10.1002/jhet.2782

Authors

Saloutina Lyudmila V. ¹ , Tretyakov Evgeny V. ² , Slepukhin Pavel A. ¹ , Saloutin Victor I. ¹ , Chupakhin Oleg N. ¹

Affiliations

1	(Данные Web of science) Postovsky Inst Organ Synth, 22-20 S Kovalevskoy Akad Skaya, Ekaterinburg 620990, Russia
2	(Данные Web of science) Vorozhtsov Inst Organ Chem, 9 Ak Lavrentiev Ave, Novosibirsk 630090, Russia

Perfluorodiacetyl (PFDA) demonstrates high-synthetic potential in reaction with bifunctional nucleophilic reagents. Therefore, PFDA is a useful reagent in the synthesis of CF3-substituted heterocycles. In this work, we explored the reaction of PFDA with a sterically hindered bis-hydroxylamine, isolated the products and clarified their structures. It was found that the reaction initially gave the 5,5,6,6-tetramethyl-2,3-bis(trifluoromethyl)pyperazine-1,2,3,4-tetraol heterocycle with a unique set of functional groups. This tetraol was shown to easily undergo dehydration with formation of the first cyclic alpha-CF3-substituted nitrone.

Saloutina L.V. , Tretyakov E.V. , Slepukhin P.A. , Saloutin V.I. , Chupakhin O.N.
Synthesis of Cyclic Vicinal Trifluoromethylated Hydroxylamine and Nitrone Based on Perfluorodiacetyl
Journal of Heterocyclic Chemistry. 2017. V.54. N3. P.1887-1890. DOI: 10.1002/jhet.2782 WOS Scopus РИНЦ

Published online:	Oct 12, 2016
Published print:	May 1, 2017

Web of science	WOS:000401732500023
Scopus	2-s2.0-84991269268
Elibrary	30984504
OpenAlex	W2530574656