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Synthesis of Cyclic Vicinal Trifluoromethylated Hydroxylamine and Nitrone Based on Perfluorodiacetyl
Author(s) -
Saloutina Lyudmila V.,
Tretyakov Evgeny V.,
Slepukhin Pavel A.,
Saloutin Victor I.,
Chupakhin Oleg N.
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2782
Subject(s) - chemistry , nitrone , hydroxylamine , reagent , steric effects , bifunctional , trifluoromethyl , vicinal , nucleophile , nucleophilic addition , bicyclic molecule , organic chemistry , cycloaddition , catalysis , alkyl
Perfluorodiacetyl (PFDA) demonstrates high‐synthetic potential in reaction with bifunctional nucleophilic reagents. Therefore, PFDA is a useful reagent in the synthesis of CF 3 ‐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 α‐CF 3 ‐substituted nitrone.