Abstract
Reactions of isolable disilynes and digermynes with alkynes can result in the formation of the corresponding disila- (DSBs) and digermabenzenes (DGBs), wherein two carbon atoms of the benzene ring are replaced by silicon or germanium atoms. Detailed structural and spectroscopic analyses of these DSBs and DGBs have revealed that they exhibit considerable aromaticity, comparable to that of benzene. However, in contrast to the all-carbon system benzene, these DSBs and DGBs are highly reactive toward small molecules such as oxygen, hydrogen, 1,3-dienes, and water. During the investigation of their reactivity, we discovered that a 1,2-DGB works as a catalyst for the cyclotrimerization of arylalkynes, which provides access to the corresponding 1,2,4-triarylbenzenes. In this perspective article, our recent progress in the area of DSB and DGB chemistry is summarized.
Highlights
Multiple-bond compounds of heavier-group-14 elements represent the heavier homologues of unsaturated organic compounds.[1]
Detailed structural and spectroscopic analyses of these DSBs and DGBs have revealed that they exhibit considerable aromaticity, comparable to that of benzene
In contrast to the all-carbon system benzene, these DSBs and DGBs are highly reactive toward small molecules such as oxygen, hydrogen, 1,3-dienes, and water
Summary
Multiple-bond compounds of heavier-group-14 elements represent the heavier homologues of unsaturated organic compounds.[1]. The extent of bond-shortening of the E]E bond relative to the corresponding single bond is not as pronounced as for the C]C bonds These structural features could be feasibly interpreted in terms of a double donor–acceptor bond (based on valence-bond theory) or socalled second-order Jahn–Teller mixing of the p- and s*orbitals (Fig. 1).[2,3] in case of heavier-group-14 elements, the term “p-bond” would be formally suitable, as it comprises np-orbitals and the mixing of orbitals, which would be different from the carbon systems. As in the case of the allcarbon systems, the corresponding benzvalene-, prismane-, and Dewar-type isomers are thermodynamically unstable relative to
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