Tetrahedron Lett., 2014, 55, 6851-6855

A.N. Kazakova, R.O. Iakovenko, V.M. Muzalevskiy, I.A. Boyarskaya, M.S. Avdontceva, G.L. Starova, A.V. Vasilyev, V.G. Nenajdenko
“Trifluoromethylated allyl alcohols: acid-promoted reactions with arenes and unusual ‘dimerization’”

Tetrahedron Lett., 2014, 55, 6851-6855

DOI: 10.1016/j.tetlet.2014.10.083


An unusual ‘dimerization’ of CF3-allyl alcohols [ArCH=CHCH(OH)CF3] under the action of anhydrous FeCl3 was found to give fluorinated indanes in 62–90% yields via the formation of intermediate allyl cations. Reactions of CF3-allyl alcohols with arenes (Ar′H) led to CF3-alkenes [Ar(Ar′)CHCH=CHCF3] in 48–75% yields. The mechanisms of the transformations are discussed.

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