Decarboxylation syntheses of some polyfluorophenyl -tin and -germanium compounds

G. B. Deacon, G. J. Farquharson

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The triphenyltin carboxylates, Ph3SnO2CR (R = C6F5,p-MeOC6F4, p-EtOC6F4, or o-HC6F4), p-(Ph3SnO2C)2C6F4.H2O, and O-(Ph3SnO2C)2C6F4.H2O have been prepared by reaction of triphenyltin hydroxide with the appropriate polyfluorocarboxylic acids in methanol. Thermal decomposition of Ph3SnO2CR (R = C6F5, p-MeOC6F4, or p-EtOC6F4) in boiling pyridine gave the corresponding polyfluorophenyltriphenyltin compounds Ph3SnR. For R = p-MeOC6F4, the yield was lowered owing to competing formation of tetraphenyltin. Similar decomposition of p-(Ph3SnO2C)2C6F4.H2O gave p-(Ph3Sn)2C6F4 (major product) and Ph3Sn-p-HC6F4, whilst o-(Ph3SnO2C)2C6F4 gave triphenyltin fluoride, and Ph3SnO2C-o-HC6F4 failed to react. Di (phenylmercuric)tetrafluoroterephthalate and tetrafluorophthalate underwent decarboxylation in boiling pyridine giving p-(PhHg)2C6F4 and o-PhgC6C6F4CO2HgPh respectively, whilst p-(Ph3PbO2C)2C6F4 gave p-(Ph3Pb)2C6F4, Ph3Pb-p-HC6F4, and tetraphenyllead. Reaction of bromotriphenylgermane with silver pentafluorobenzoate in boiling pyridine gave pentafluorophenyltriphenylgermane, but analogous reactions with silver p-ethoxytetrafluorobenzoate and disilver tetrafluoroterephthalate gave, after work up, mixtures of polyfluorophenylgermanes, Ph4Ge, and (Ph3Ge)2O.

Original languageEnglish
Pages (from-to)73-90
Number of pages18
JournalJournal of Organometallic Chemistry
Issue number1
Publication statusPublished - 26 Jul 1977

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