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Synthesis of trifluoromethylnaphthalenes

Synthesis of trifluoromethylnaphthalenes
Synthesis of trifluoromethylnaphthalenes
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.
grignard reagents, naphthalenes, trifluoromethylketones photochemical trifluoromethylation, carbonyl-compounds, aromatic-compounds, grignard-reagents, organic-synthesis, convenientmethod, ketones, reactivity, halides, indium
0040-4020
10067-10074
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
El-Sagheer, A. H.
c37c0aa8-20a2-4fd9-b2cf-3a891182db00
El-Tamany, E. S. H.
e500b10f-b3bd-4548-b0dd-bf05b4e83076
Metwally, R. N.
a7f9438f-cd8f-476e-a72e-e00cd89926e3
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
El-Sagheer, A. H.
c37c0aa8-20a2-4fd9-b2cf-3a891182db00
El-Tamany, E. S. H.
e500b10f-b3bd-4548-b0dd-bf05b4e83076
Metwally, R. N.
a7f9438f-cd8f-476e-a72e-e00cd89926e3

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

Record type: Article

Abstract

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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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

Catalogue record

Date deposited: 16 Dec 2005
Last modified: 15 Jul 2019 19:28

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