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Issue 2, 2012
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The addition of amides to group 14 (di)-metallenes

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Abstract

The addition of a series of primary and secondary amides to the group 14 (di)metallenes Mes2Si[double bond, length as m-dash]SiMes2, Mes2Ge[double bond, length as m-dash]GeMes2 and (Me3Si)2Si[double bond, length as m-dash]C(OSiMe3)R, where R = t-Bu or R = 1-Ad, was examined. In general, the addition of primary and N-methyl amides gave amide adducts whereas the addition of N-phenyl amides gave imidate adducts. The regiochemistry of the additions was highly dependent upon the substituent bonded to the amide nitrogen. We propose that the formation of the adducts proceeds by way of a zwitterionic intermediate. The reactivity of tetramesityldigermene towards amides is used to predict the structure of the amide adducts formed on the Ge(100)-2 × 1 surface.

Graphical abstract: The addition of amides to group 14 (di)-metallenes

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Article information


Submitted
01 Aug 2011
Accepted
06 Sep 2011
First published
09 Nov 2011

Dalton Trans., 2012,41, 609-621
Article type
Paper

The addition of amides to group 14 (di)-metallenes

J. A. Hardwick, L. C. Pavelka and K. M. Baines, Dalton Trans., 2012, 41, 609
DOI: 10.1039/C1DT11450F

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