Fused Tricyclic Disilenes with Highly Strained SiSi Double Bonds: Addition of a SiSi Single Bond to a SiSi Double Bond

Tanaka, Ryoji; Iwamoto, Takeaki; Kira, Mitsuo

doi:10.1002/anie.200602214

Cited by 44 publications

(31 citation statements)

References 19 publications

(22 reference statements)

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“…However, the reduction of tetrabromides (2 S *, 2 S *)- 41 and (2 R *, 2 S *)- 41 with KC 8 affords unexpectedly fused tricyclic disilenes trans - 42 and cis - 42 , respectively (eqs [18] and [19]). 51) …”

Section: Other Stable Disilenesmentioning

confidence: 99%

Bonding and structure of disilenes and related unsaturated group-14 element compounds

Kira

2012

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

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Structure and properties of silicon-silicon doubly bonded compounds (disilenes) are shown to be remarkably different from those of alkenes. X-Ray structural analysis of a series of acyclic tetrakis(trialkylsilyl)disilenes has shown that the geometry of these disilenes is quite flexible, and planar, twist or trans-bent depending on the bulkiness and shape of the trialkylsilyl substituents. Thermal and photochemical interconversion between a cyclotetrasilene and the corresponding bicyclo[1.1.0]tetrasilane occurs via either 1,2-silyl migration or a concerted electrocyclic reaction depending on the ring substituents without intermediacy of the corresponding tetrasila-1,3-diene. Theoretical and spectroscopic studies of a stable spiropentasiladiene have revealed a unique feature of the spiroconjugation in this system. Starting with a stable dialkylsilylene, a number of elaborated disilenes including trisilaallene and its germanium congeners are synthesized. Unlike carbon allenes, the trisilaallene has remarkably bent and fluxional geometry, suggesting the importance of the π-σ* orbital mixing. 14-Electron three-coordinate disilene-palladium complexes are found to have much stronger π-complex character than related 16-electron tetracoordinate complexes.

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Section: Other Stable Disilenesmentioning

confidence: 99%

Bonding and structure of disilenes and related unsaturated group-14 element compounds

Kira

2012

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

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“…This results in a large red-shift of the longest wavelength UVvis absorption for trans-9, while the UVvis of cis-9 is very similar to that of 1 (cis-9: max = 433 nm; trans-9: max = 517 nm). 25 Apart from the obvious synthetic potential Si=Si bonds bring about, the conformational flexibility and the inherently smaller HOMOLUMO gap are strong arguments for the incorporation of Si=Si units into both inorganic and organic conjugated materials. As will be summarized in the following, disilenides, i.e., disila analogs of vinyl anion synthons, are suitable as generally applicable Si=Si transfer reagents.…”

Section: ç Introductionmentioning

confidence: 99%

The Versatile Chemistry of Disilenides: Disila Analogues of Vinyl Anions as Synthons in Low-valent Silicon Chemistry

Scheschkewitz

2010

Chemistry Letters

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Since the first isolation of a disila analog to vinyl anion synthons, namely lithium disilenide Tip 2 Si=Si(Tip)Li (Tip: 2,4,6-triisopropylphenyl), the number of available disilenides and their synthetic applications have rapidly expanded. Derivatives with aryl, silyl, alkyl, and hydrogen substituents have been reported and even one cyclic derivative is available. Disilenides can be used to introduce the Si=Si unit to a variety of organic and inorganic substrates. Depending on whether products feature sufficiently reactive residual functionality, the Si=Si bond is either retained or undergoes further (so far intramolecular) transformations. Heteroatom-substituted disilenes are easily accessible via disilenides. Using Tip 2 Si=Si(Tip)Li as a starting material, for instance, a variety of otherwise inaccessible compounds can be prepared: conjugated systems with more than one Si=Si unit, © 1 -transition-metal complexes, functional homo-and heteronuclear silacycles, and molecular silicon clusters with substituent-free vertices. In this review article, an account on the chemistry of disilenides is given.

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“…Historically, the first thermally stable Disilene molecule containing silicon-silicon double bond was synthesized in 1981 [11][12]. In recent experiments of silicon deposition on silver substrates under ultra high vacuum (UHV) we have shown the first evidence of silicene formation with a honeycomb graphene-like structure forming either parallel assembly of one-dimensional nano-ribbons (NRs) or highly ordered sheet of silicene [13][14][15][16][17][18][19][20][21][22][23][24][25].…”

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Silicene structures on silver surfaces

Enriquez¹,

Vizzini²,

Kara³

et al. 2012

J. Phys.: Condens. Matter

169

170

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In this paper we report on several structures of silicene, the analog of graphene for silicon, on the silver surface Ag(100), Ag(110) and Ag(111). Deposition of Si produces honeycomb structures on these surfaces. In particular, we present an extensive theoretical study of silicene on Ag(111) for which several recent experimental studies were published. Different silicene structures were obtained only by varying the silicon coverage and/or its atomic arrangement.All the studied structures show that silicene is buckled with a Si-Si nearest neighbor distance varying between 2.28 Å and 2.5Å. Due to the buckling in the silicene sheet, the apparent (lateral) Si-Si distance can be as low as 1.89 Å. We also found that for a given coverage and symmetry, one may observe different STM images corresponding to structures that differ by only a translation.

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Fused Tricyclic Disilenes with Highly Strained SiSi Double Bonds: Addition of a SiSi Single Bond to a SiSi Double Bond

Cited by 44 publications

References 19 publications

Bonding and structure of disilenes and related unsaturated group-14 element compounds

Bonding and structure of disilenes and related unsaturated group-14 element compounds

The Versatile Chemistry of Disilenides: Disila Analogues of Vinyl Anions as Synthons in Low-valent Silicon Chemistry

Silicene structures on silver surfaces

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