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.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/S0040-4020(00)00977-7
Related URLs:
Keywords: grignard reagents, naphthalenes, trifluoromethylketones photochemical trifluoromethylation, carbonyl-compounds, aromatic-compounds, grignard-reagents, organic-synthesis, convenientmethod, ketones, reactivity, halides, indium
Subjects: Q Science
Q Science > QD Chemistry
Divisions : University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 18866
Accepted Date and Publication Date:
15 December 2000Published
Date Deposited: 16 Dec 2005
Last Modified: 31 Mar 2016 11:35

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