Abstract
Abstract Reaction of bromodifluoromethyl phosphonate 3 with zinc and propynyl chloride led to allenyl phosphonate 4 which was brominated to give dibromophosphonate 6. Alkylation of adenine 7 with 6 afforded Z- and E- difluorophosphonates 8 and 9. Hydrogenation of 8 furnished saturated difluorophosphonate 10a which was dealkylated to the corresponding phosphonic acid 10b. Reaction of 8 with tetrabutylammonium fluoride gave fluoroenyne phosphonate 11 whereas 9 and 1,5-diazabicyclo[4.3.0]non-5-ene furnished bromofluorodiene phosphonate 16. Hydrogenation of 11 afforded phosphonates 13 and 14 in addition to defluorinated product 15.
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