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
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
15 December 2000
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), .
(doi:10.1016/S0040-4020(00)00977-7).
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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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: 15 Mar 2024 06:08
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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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