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2005
Furan derivatives
R 0060
Manganese(III) Acetate Mediated Synthesis of 3-Trifluoroacetyl-4,5-dihydroand 3-(Dihydrofuran-2(3H)-ylidene)-1,1,1-trifluoroacetones by Free
35- 118 furans
Radical Cyclization. Part 1. — The transition metal salt mediated oxidative addition
of 1,3-dicarbonyl compounds to unsaturated systems is applied to the Mn(O-Ac)3
mediated reaction of trifluormethyl-1,3-dicarbonyl compounds (II) with conjugated
alkenes (I) and (IV). The radical cyclization conditions are optimized with respect to
effects of solvents on product yields. Generally, higher yields are obtained with 1,1-disubstituted alkenes, cf. formation of (IIIe). The formation of trifluoroacetones (VI) may
be the result of an alkyl substituent at the 2-position of the alkene, cf. (IV). A reaction
mechanism is proposed. — (YILMAZ*, M.; PEKEL, A. T.; J. Fluorine Chem. 126
(2005) 3, 401-406; Dep. Chem., Fac. Sci., Ankara Univ., TR-06100 Ankara, Turk.;
Eng.) — H. Hoennerscheid
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