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2004
Organo-phosphorus compounds
S 0080
Syntheses of α-Fluoro-α,β-Unsaturated Thioamides and Thiazolines from a
— An efficient synthesis of fluorophosphonodithio46- 169 Fluorophosphonodithioacetate.
acetate (II) by defluorination of the corresponding difluoro analogue (I) with Et-SLi
is presented. Although dithioacetate (II) is not a suitable starting compound for
Horner—Wadsworth—Emmons reaction, the corresponding thioamides (XII) and
(XVI) as well as thiazoline derivative (IV) are successfully applied to olefination reactions with various aldehydes. The E/Z-selectivity is strongly influenced by the nature
of thioamide resp. thiazoline. Best results are achieved with the thiazoline (IV). —
(PFUND, E.; MASSON, S.; VAZEUX, M.; LEQUEUX*, T.; J. Org. Chem. 69 (2004)
14, 4670-4676; Lab. Chim. Mol. Thio-Org., CNRS, Inst. Sci. Matiere Rayonnem.,
Univ. Caen, F-14050 Caen, Fr.; Eng.) — Mischke
2004
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