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Synthesis 2010(23): 4096-4100  
DOI: 10.1055/s-0030-1258280
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Solvent-Free Stereoselective Synthesis of (E)-Trifluoromethyl Imines and Hydrazones

Laura Carroccia, Stefania Fioravanti*, Lucio Pellacani*, Paolo A. Tardella*
Dipartimento di Chimica, Università degli Studi di Roma ‘La Sapienza’, P. le Aldo Moro 5, 00185 Rome, Italy
Fax: +39(06)490631; e-Mail: lucio.pellacani@uniroma1.it; e-Mail: stefania.fioravanti@uniroma1.it;
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Publication History

Received 12 July 2010
Publication Date:
01 October 2010 (online)

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Abstract

A new, green and efficient strategy for the synthesis of trifluoromethyl ketimines, aldimines, and hydrazones starting from the corresponding trifluoromethyl carbonyl compounds or their hemiacetals is reported. The condensation reactions were performed under solvent-free conditions with a range of amines or hydrazines and proceeded with high stereoselectivity, always giving only the E-isomer in very good yields.

Key words

fluorinated compounds - imines - hydrazones - stereo­selectivity - condensation

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The synthesis of 19 under solvent-free conditions gave the expected product in very low yields, probably because
p-nitrophenylhydrazine is a solid compound.