Trifluoromethylated Vinylic and Aromatic Compounds from α-(Trifluoro­methyl)allyl Alcohols

Sylvie Radix-Large; Stéphanie Kucharski; Bernard R. Langlois

doi:10.1055/s-2004-815928

FEATUREARTICLE

Trifluoromethylated Vinylic and Aromatic Compounds from α-(Trifluoromethyl)allyl Alcohols

Sylvie Radix-Large, Stéphanie Kucharski, Bernard R. Langlois*
Université Claude Bernard-Lyon I, Laboratoire SERCOF (UMR 5181), 43 Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex (France)
Fax: +33(4)72431323; e-Mail: Bernard.Langlois@univ-lyon1.fr;

Abstract

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Abstract

α-(Trifluoromethyl)allyl alcohols, easily available from α,β-unsaturated carbonyl compounds, are readily converted into γ-(trifluoromethyl)allyl thioethers, benzyl ethers, trifluoroacetates, and azides. A phenyl substituent at the γ-position to the hydroxyl function enhances their reactivity and the ease of S_N2′ or S_N1′ substitutions, whereas a phenyl ring at the α-position allows the BF₃-mediated synthesis of (trifluoromethyl)indenes. 4-Alkyl-4-methoxy-1-(trifluoromethyl)cyclohexa-2,5-dienols, readily available from 4-alkylphenols, are easily converted to 4-alkyl(trifluoromethyl)benzenes bearing a nucleophilic substituent (MeO, Cl) either on the ring or the benzylic position.

Key words

1-(trifluoromethyl)allyl alcohols - 3-(trifluoromethyl)allyl compounds - (trifluoromethyl)arenes - (trifluoromethyl)indenes - allylic substitution

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Trifluoromethylated Vinylic and Aromatic Compounds from α-(Trifluoro­methyl)allyl Alcohols

Trifluoromethylated Vinylic and Aromatic Compounds from α-(Trifluoromethyl)allyl Alcohols