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Cyanide Initiated Perfluoroorganylations with Perfluoroorgano Silicon Compounds by Patricia Panne; Dieter Naumann; Berthold Hoge is a Chemistry article available to read on EtoBox.

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Cyanophenylphosphanes, Ph 2 PCN or PhP(CN) 2 , do not react with Me 3 SiCF 3 or Me 3 SiC 6 F 5 in the absence of cyanide ions. Catalytic amounts of ionic cyanides such as [NEt 4 ]CN, [18-crown-6-K]CN or NaCN initiate per ̄uoroorganylation reactions. The tri ̄uoromethylphosphines, Ph 2 PCF 3 and PhP(CF 3 ) 2 , as well as the penta ̄uorophenylphosphines, Ph 2 PC 6 F 5 and PhP(C 6 F 5 ) 2 , are isolated in 60±75% yield. In dimethylformamide or acetone solutions, side reactions are observed while reactions in CH 2 Cl 2 and acetonitrile proceed selectively. Me 3 SiCF 3 addition to the carbonyl groups of dimethylformamide and acetone occurs on treatment of Me 3 SiCF 3 solutions of these solvents with catalytic amounts of cyanide, cyanate or thiocyanate salts even at low temperature. The formation of the reactive silicate [Me 3 Si(CN)CF 3 ] À in reactions with an excess of [18-crown-6-K]CN is proved by low temperature NMR investigations.

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Author

Patricia Panne; Dieter Naumann; Berthold Hoge

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-1139)

Published

2001

Language

EN

Field

Chemistry (Physical Sciences)