New trends in the chemistry of aromatic compounds with fluorine-containing substituents
1995; Elsevier BV; Volume: 72; Issue: 2 Linguagem: Inglês
10.1016/0022-1139(94)00411-8
ISSN1873-3328
AutoresL. M. YAGUPOL'SKII, Yurii L. Yagupolskii,
Tópico(s)Chemical Reactions and Mechanisms
ResumoRecently, new methods for the introduction of fluorine-containing substituents into aromatic compounds have been developed in our Department and new types of organic substances synthesized. Emphasis has been placed not only on the ‘classic’ groups, such as the fluorine atom or perfluoro-alkyl and -alkenyl fragments, but mainly on substituents with perfluoroalkyl groups separated from the nuclei by the heteroatoms oxygen, sulfur (in valency states 2, 4 and 6), nitrogen and metals. We have also developed new principles for the construction of super-strong electron-withdrawing substituents and super-strong acids. This approach consists in replacing the sp2-oxygen atom in various groups with the =NSO2CF3 radical and has been confirmed by examples of substituents with the central atoms consisting of sulfur in different valence states, carbon, phosphorus and iodine. From this principle, a stable substituent with σp constant 1.76, equal to three nitro groups in its influence towards benzene nuclei, has been constructed.
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