A synthesis of trifluoromethyl-substituted naphthalenes

Mellor, John M., El-Sagheer, Afaf H. and Salem Eedm, Ezz El-Din M. (2000) A synthesis of trifluoromethyl-substituted naphthalenes Tetrahedron Letters, 41, (38), pp. 7383-7386. (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.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/S0040-4039(00)01254-5
ISSNs: 0040-4039 (print)
Keywords: additions, grignard reagents, naphthalenes, trifluoromethylketones grignard-reagents, carbonyl-compounds
ePrint ID: 18864
Date :
Date Event
16 September 2000Published
Date Deposited: 15 Dec 2005
Last Modified: 16 Apr 2017 23:08
Further Information:Google Scholar
URI: http://eprints.soton.ac.uk/id/eprint/18864

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