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Synthesis and Chemistry of Novel Perhalogenated Imines, Oxaziridines, and Oxazolidines
Author(s) -
Mlsna Todd E.,
Young Jennifer A.,
DesMarteau Darryl D.
Publication year - 2002
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/1521-3749(200208)628:8<1789::aid-zaac1789>3.0.co;2-n
Subject(s) - chemistry , imine , hexafluoroacetone , lewis acids and bases , oxazolidine , polymer chemistry , medicinal chemistry , organic chemistry , catalysis
Imines have been prepared using three different methods. The thermal addition of tetrafluoroethylene to N‐bromoperhalo‐1‐alkanimines (R f CF=NBr) to give imines of the type R f CF=NCF 2 CF 2 Br, the Lewis acid cleavage of perfluorinated amines to give imines of the type R f N=CFR f ′ and the one pot reaction between hexafluoroacetone and perfluoroamides. Reactions of these imines with m‐chloroperoxy benzoic acid (MCPBA) lead to the corresponding cis ‐perfluoro‐2, 3‐dialkyloxaziridines R f $\overline{N-O-CF}$ R F ′. The oxaziridines undergo cycloadditions with olefins to give the corresponding oxazolidines. A preliminary investigation was done on the synthesis and reaction chemistry of complex formed between activated zinc and the 4‐iodo and 4‐bromo‐perhalooxazolidines.