Mellor, John M., El-Sagheer, Afaf H. and Salem Eedm, Ezz El-Din M.
A synthesis of trifluoromethyl-substituted naphthalenes
Tetrahedron Letters, 41, (38), . (doi:10.1016/S0040-4039(00)01254-5).
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Alkyl and aryl Grignard reagents add to 1-(3,4-dihydro-2H-5-pyranyl)-2,2,2-trifluoro-1-ethanone by 1,4-addition, but benzyl Grignard reagents react in good yield by 1,2-addition. Dehydration of the resulting alcohols affords intermediate dienes, which readily undergo cyclisation to give substituted trifluoromethylnaphthalenes. Addition to other trifluoromethylketones permits access to a range of novel fluorinated naphthalenes and benzenes.
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