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2005
Thioethers
P 0430
35- 070
A New Strategy for the Synthesis of Highly Functionalized Fluorinated Compounds by Reaction of Lithium Dianions of Carboxylic Acids with Perfluoroketene Dithioacetals. — Lithium dianions from carboxylic acids, α,β-unsaturated carboxylic acids, aromatic and heteroaromatic acids are added to perfluoroketene dithioacetal (II). The reaction affords the corresponding α-trifluoromethyl γ- or ε-dicarboxylic acid derivatives where one carboxylic function is masked. In the case of dianions
derived from unsaturated carboxylic acids, the addition step proceeds regioselectively
through the γ-position of the dienolate. However, an important amount of the adduct
undergoes migration of the double bond leading to compounds (V) and (VI). —
(SOTOCA, E.; BOUILLON, J.-P.; GIL, S.; PARRA, M.; PORTELLA*, C.;
Tetrahedron 61 (2005) 18, 4395-4402; Lab. "React. Sel. Appl.", CNRS, Fac. Sci.,
Univ. Reims-Champagne-Ardenne, F-51687 Reims, Fr.; Eng.) — Bartels
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