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Synthesis of trifluoromethylnaphthalenes

Record type: Article

Reaction of 1-(3,4-dihydro-2H-5-pyranyl)-2,2,2-trifluoro-1-ethanone with benzylic Grignard reagents affords by 1,2-addition unsaturated allylic alcohols. These alcohols readily undergo dehydration and cyclisation to give trifluoromethylnaphthalenes. The generality of this procedure was established by reaction with diverse benzyl and allyl Grignard reagents and by reaction of a number of unsaturated ketones. The resulting trifluoromethylnaphthalenes were oxidised to give substituted acetic- and propionic acids.

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Citation

Mellor, J. M., El-Sagheer, A. H., El-Tamany, E. S. H. and Metwally, R. N. (2000) Synthesis of trifluoromethylnaphthalenes Tetrahedron, 56, (51), pp. 10067-10074. (doi:10.1016/S0040-4020(00)00977-7).

More information

Published date: 15 December 2000
Keywords: grignard reagents, naphthalenes, trifluoromethylketones photochemical trifluoromethylation, carbonyl-compounds, aromatic-compounds, grignard-reagents, organic-synthesis, convenientmethod, ketones, reactivity, halides, indium

Identifiers

Local EPrints ID: 18866
URI: http://eprints.soton.ac.uk/id/eprint/18866
ISSN: 0040-4020
PURE UUID: 2d547472-cb82-4bbf-9a04-5b558f83663c

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Date deposited: 16 Dec 2005
Last modified: 17 Jul 2017 16:34

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Contributors

Author: J. M. Mellor
Author: A. H. El-Sagheer
Author: E. S. H. El-Tamany
Author: R. N. Metwally

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