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), 10067-10074. (doi:10.1016/S0040-4020(00)00977-7).
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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.
|Digital Object Identifier (DOI):||doi:10.1016/S0040-4020(00)00977-7|
|Keywords:||grignard reagents, naphthalenes, trifluoromethylketones photochemical trifluoromethylation, carbonyl-compounds, aromatic-compounds, grignard-reagents, organic-synthesis, convenientmethod, ketones, reactivity, halides, indium|
Q Science > QD Chemistry
|Divisions:||University Structure - Pre August 2011 > School of Chemistry
|Date Deposited:||16 Dec 2005|
|Last Modified:||06 Aug 2015 02:18|
|RDF:||RDF+N-Triples, RDF+N3, RDF+XML, Browse.|
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