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Issue 4, 2016
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Reactivity in the periphery of functionalised multiple bonds of heavier group 14 elements

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Heavier group 14 multiple bonds have intrigued chemists since more than a century. The synthesis of stable compounds with double and triple bonds with silicon, germanium, tin and lead had considerable impact on modern ideas of chemical bonding. These developments were made possible by the use of bulky substituents that provide kinetic and thermodynamic protection. Since about a decade the compatibility of heavier multiple bonds with various functional groups has moved into focus. This review covers multiply bonded group 14 species with at least one additional reactive site. The vinylic functionalities of groups 1 and 17, resulting in nucleophilic and electrophilic disila vinyl groups, respectively, are the most prevalent and well-studied. They have been employed repeatedly for the transfer of heavier multiple bonds to yield low-valent group 14 compounds with novel structural motifs. Vinylic functionalities of groups 2 to 16 and a few σ-bonded transition metal complexes are experimentally known, but their reactivity has been studied to a lesser extent. Donor-coordinated multiple bonds are a relatively new field of research, but the large degree of unsaturation as isomers of alkynes (as well as residual functionality in some cases) offers considerable possibility for further manipulation, e.g. for the incorporation into more extended systems. Heavier allyl halides constitute the major part of heavier multiple bonds with a functional group in allylic position and some examples of successful transformations are given. At present, remote functionalities are basically limited to para-phenylene functionalised disilenes. The reported use of the latter for further derivatisation might encourage investigations in this direction. In summary, the study of peripherally functionalised multiple bonds with heavier group 14 elements is already well beyond its infancy and may be an instrumental factor in awakening the potential of group 14 chemistry for applications in polymers and other materials.

Graphical abstract: Reactivity in the periphery of functionalised multiple bonds of heavier group 14 elements

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The article was received on 17 Sep 2015 and first published on 27 Oct 2015

Article type: Review Article
DOI: 10.1039/C5CS00720H
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Chem. Soc. Rev., 2016,45, 900-921

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    Reactivity in the periphery of functionalised multiple bonds of heavier group 14 elements

    C. Präsang and D. Scheschkewitz, Chem. Soc. Rev., 2016, 45, 900
    DOI: 10.1039/C5CS00720H

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