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  • Title: Synthesis of trifluoromethyl-substituted arenes, cyclohexenones and pyran-4-ones by cyclocondensation of 1,3-bis(silyloxy)-1,3-butadienes with 4,4-dimethoxy-1,1,1-trifluorobut-3-en-2-one: influence of the lewis acid on the product distribution.
    Author: Bunescu A, Reimann S, Lubbe M, Spannenberg A, Langer P.
    Journal: J Org Chem; 2009 Jul 17; 74(14):5002-10. PubMed ID: 19480453.
    Abstract:
    The TiCl(4)-mediated formal [3 + 3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 4,4-dimethoxy-1,1,1-trifluorobut-3-en-2-one afforded a variety of functionalized 4-methoxy-6-(trifluoromethyl)salicylates and 3-methoxy-5-(trifluoromethyl)phenols with very good regioselectivity. The Me(3)SiOTf-mediated cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes, containing no substituent located at carbon atom C-4 of the diene (R(1) = H), resulted in the formation of trifluoromethyl-substituted pyran-4-ones. In contrast, trifluoromethylated cyclohexenones were formed when dienes were employed which do contain a substituent located at carbon C-4 (R(1) not equal H).
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