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TRANSFORMATION OF ORGANOPHOSPHORUS S-TRIFLUOROMETHYLTHIOATES RR'P(O)SCFs INTO FLUORIDATES RR'P(0)F3 STEREOCHEMICAL ASPECTS OF THIOCARBONYL FLUORIDE EXTRUSION |
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| Authors: | Andrzej Łopusiński |
| Institution: | Polish Academy of Sciences, Centre of Molecular and Macromolecular Studies , Sienkiewicza 112, Lód? , Poland |
| Abstract: | Abstract The stereochemical course of the thermal or by nucleophiles catalyzed extrusion reaction of thiocarbonyl fluoride from Two diastereoisomeric (6) and optically active (10) organophosphorus S-trifluoromethylthioates has been investigated. To explain the observed retention of configuration at phosphorus in fluoridates 7 formed in the thermal reactions, a four center transition state for such reactions has been proposed. The lack of the stereoselectivity in the catalyzed reactions of 6, and the observed racemization of the final product 11 are briefly discussed. |
| Keywords: | O O-dialkyl-S-trifluoromethyl phosphorothioate cis- and trans-2-S-trifluoromethyl-2-oxo-4-methyl-1 2 2-dioxaphosphorinans cis- and trans-2-fluoro-2-oxo-4-methyl-1 3 2-dioxaphosphorinans optically active t-butyl(pheny1)-S-trifluoromethyl phosphinothioate dialkylphosphorofluoridate |