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).


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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
ISSNs: 0040-4020 (print)
Keywords: grignard reagents, naphthalenes, trifluoromethylketones photochemical trifluoromethylation, carbonyl-compounds, aromatic-compounds, grignard-reagents, organic-synthesis, convenientmethod, ketones, reactivity, halides, indium
ePrint ID: 18866
Date :
Date Event
15 December 2000Published
Date Deposited: 16 Dec 2005
Last Modified: 16 Apr 2017 23:08
Further Information:Google Scholar

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