Synthesis 2009(7): 1190-1194  
DOI: 10.1055/s-0028-1083371
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Reaction of N-Nonaflylbenzotriazole with Silyl Enol Ethers

Moritz Uhde, Thomas Ziegler*
Institute of Organic Chemistry, University of Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany
Fax: +49(7071)295244; e-Mail: thomas.ziegler@uni-tuebingen.de;
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Publikationsverlauf

Received 9 October 2008
Publikationsdatum:
11. Februar 2009 (online)

Abstract

N-Nonaflylbenzotriazole reacts with trimethylsilyl enol ethers in tetrahydrofuran at room temperature under tetrabutylammonium fluoride catalysis to afford o-(nonafluorobutylsulfonamido)phenylhydrazones in 19-82% yield. N-Nonaflylbenzotriazole reacts twice with the less sterically demanding silyl enol ethers to afford the corresponding o-(nonafluorobutylsulfonamido)phenyl­azo enols in 41-75% yield.