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Formation of Germanium-Nitrogen Double Bonds in Reactions of the Electron-rich Germylene Bisgermanium(II) with a Range of Diazo-compounds

DOI: 10.1039/DT9870000501

Source and publish data:

Journal of the Chemical Society, Dalton Transactions p. 501 - 508 (1987)

Update date:2022-08-05

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Authors:

Glidewell, ChristopherGlidewell, Christopher

Lloyd, DouglasLloyd, Douglas

Lumbard, Keith W.Lumbard, Keith W.

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Article abstract of DOI:10.1039/DT9870000501

The electron-rich germylene Ge2 reacts with the diazo-compounds R1CH2COC(N2)R2 1 = H, R2 = CO(OEt), SO2C6H4Me-p, or COPh; R1, R2 = -CMe2CH2C(O)->, which contain an enolisable function, to yield the heterocycles ; the weakly acidic diazo-compounds ethyl diazoacetate and diazoacetophenone yield bis-adducts Ge2 (R = OEt or Ph).Diazo-compounds containing two non-enolisable substituents yield mono-adducts with Ge2 which can be hydrolysed to yield the diol Ge(OH)22 and, in one example, the corresponding hydrazone H2NN=C(COPh)CO(OEt).These adducts appear to be thermodinamically stable in an aprotic solvent, but can be trapped by addition of ethanol, to yield Ge2(OEt)2>, or of diazoacetophenone to yield Ge<(SiMe3)2>22>.All the reactions of the germylene with diazo-compounds can be rationalised in terms of the initial formation of a germyleneazine <(Me3Si)2N>2Ge=N-N=C(X)Y, which readily adds any available protic species to give a germane derivative.MNDO calculations on model systems are in accord with the experimental findings and also explain their differences from results previously obtained using the simpler germylene GePh2.

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