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ChemInform Abstract: Straightforward Synthesis of 1-Alkyl-2-(trifluoromethyl)aziridines Starting from 1,1,1-Trifluoroacetone.

✍ Scribed by Sara Kenis; Matthias D'hooghe; Guido Verniest; Vinh Duc Nguyen; Tuyet Anh Dang Thi; Tuyen Van Nguyen; Norbert De Kimpe

Publisher: John Wiley and Sons
Year: 2012
Weight: 45 KB
Volume: 43
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.201213118

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✦ Synopsis

Straightforward Synthesis of 1-Alkyl-2-(trifluoromethyl)aziridines Starting from 1,1,1-Trifluoroacetone.

-The straightforward approach towards the synthesis of aziridines (IV) starts from trifluoroacetone (I) via imination, α-chlorination, hydride reduction, and ring closure. Additional information concerning the reactivity of these compounds is achieved by treatment of (IV) with acetic acid and alkyl iodides (V). In the latter case novel primary β-iodo amines, cf. (VI), are obtained through regioselective ring opening of intermediate aziridinium salts, whose synthetic potential is shown by converting them into novel α-trifluoromethyl-β-phenylethylamines (VIII).

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