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Synthesis of trifluoromethylnaphthalenes

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).

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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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


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

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