[reaction: see text] Selanylated difluoromethylphosphonates and difluoromethylphosphonothioates are good precursors to phosphonodifluoromethyl and phosphonothiodifluoromethyl radicals, respectively. When generated in the presence of alkenes and a hydrogen donor, the corresponding alpha,alpha-difluorinated alkylphosphonates or alkylphosphonothioates are produced in fair to good yields. The use of alkynes results in the formation of alpha,alpha-difluorinated allyl derivatives in useful yields. The presence of the sulfur atom in phosphonothiodifluoromethyl radicals usually translates into higher isolated yields.
Organo-phosphorus compounds S 0080 Phosphonodifluoromethyl and Phosphonothiodifluoromethyl Radicals. Generation and Addition onto Alkenes and Alkynes. -Treatment of the selenides (I) and (VII) with AIBN results in formation of the title radicals. They smoothly react with alkenes and terminal alkynes to afford difluorinated phosphonates or phosphonothioates. These compounds are of synthetic and biological interest. -(PIGNARD, S.; LOPIN, C.; GOUHIER, G.; PIETTRE*, S. R.; J. Org. Chem. 71 (2006) 1, 31-37; Lab. Fonct. Azotees Oxygenees Complexes, Inst. Rech. Chim. Org. Fine, Univ. Rouen, F-76821 Mont-Saint-Aignan, Fr.; Eng.) -Jannicke 22-178
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