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Journal article

Heterosubstituted or functionalized derivatives of 1- and 2-(trifluoromethyl)naphthalenes emanating from aryne adducts

More than two dozen new CF3-substituted naphthalene derivs. were prepd. in an expedient way by employing 3- and 4-(trifluoromethyl)benzyne as the key intermediates. 2- And 4-Chlorobenzotrifluoride were treated with butyllithium and the organometallic species thus generated were allowed to decomp. in the presence of furan. The resulting cycloadducts were reduced to the (trifluoromethyl)naphthalenes, ring-opened to the (trifluoromethyl)naphthols and transformed to the dibromo adducts. The latter were stereoselectively converted into the bromo-1,4-epoxy-1,4-dihydro(trifluoromethyl)naphthalenes and, by deoxygenation, into various bromo(trifluoromethyl)naphthalenes. Trifluoromethyl substituted naphthoic acids were obtained when the bromo compds. were subjected to a halogen/metal permutation followed by carboxylation. [on SciFinder (R)]

    Keywords: naphthalene trifluoromethyl functionalized prepn

    Note:

    CAN 143:26348

    25-24

    Benzene, Its Derivatives, and Condensed Benzenoid Compounds

    Institut des Sciences Chimiques (ISIC-BCh),Ecole Polytechnique Federale,Lausanne,Switz.

    Journal

    0039-7881

    written in English.

    88-16-4 (2-Chlorobenzotrifluoride); 98-56-6 (4-Chlorobenzotrifluoride); 110-00-9 (Furan) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of heterosubstituted or functionalized derivs. of 1- and 2-(trifluoromethyl)naphthalenes from aryne adducts); 19061-34-8P; 853017-48-8P; 853017-49-9P; 853017-50-2P; 853017-51-3P; 853017-52-4P; 853017-53-5P; 853017-54-6P; 853017-55-7P; 853017-56-8P; 853017-57-9P; 853017-58-0P (2-Bromo-5-(trifluoromethyl)naphthalene); 853017-59-1P (7-Bromo-1-trifluoromethylnaphthalene); 853017-60-4P (2-Bromo-6-trifluoromethylnaphthalene); 853017-61-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of heterosubstituted or functionalized derivs. of 1- and 2-(trifluoromethyl)naphthalenes from aryne adducts); 581-90-8P (2-Trifluoromethylnaphthalene); 26458-04-8P (1-Trifluoromethylnaphthalene); 33533-45-8P; 33533-46-9P; 33533-47-0P (8-Trifluoromethylnaphthalen-1-ol); 50318-08-6P; 853017-62-6P; 853017-63-7P; 853017-64-8P; 853017-65-9P; 853017-66-0P (5-Trifluoromethyl-2-naphthoic acid); 853017-67-1P (8-Trifluoromethyl-2-naphthoic acid); 853017-68-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of heterosubstituted or functionalized derivs. of 1- and 2-(trifluoromethyl)naphthalenes from aryne adducts)

    Reference

    Record created on 2006-03-03, modified on 2016-08-08

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