Bi(CF3)(3)/Cu(OCOCH3)(2) - a new system for the synthesis of 2-trifluoromethylcycloalkan-1-ones, trifluoromethylanilines and phenyl(trifluoromethyl) sulfane

Bi(CF3)(3) reacts in the presence of equimolar amounts of Cu(OCOCH3)(2) and 1-morpholinocyclopentene to give 1-morpholino-2-trifluoromethylcyclopenten e in 83% yield. This compound as well as intermediately formed 1-morpholino -2-trifluoromethylcyclohexen can easily be converted into the corresponding cycloketones (78 and 41% yield) using the Swarts procedure. In absence of a copper(II) source, no reactions were observed. The reaction of the system Bi(CF3)(3)/Cu(OCOCH3)(2) with N,N-diethylaniline gave an 1.7: 1 isomer mixture of 2-trifluoromethyl and 4-trifluormethyl-N, N-diethylanilines in 48% yield. With tetrabutylammonium thiophenolate, mixtures of phenyl(trifluoromethyl)s ulfane and diphenyldisulfane were obtained. Mechanisms are discussed. (C) 2 000 Elsevier Science S.A. All rights reserved.