The addition of carbonyl compounds to tetramesitylgermasilene and dimesitylgermylene

Baines, Kim M.; Cooke, Jeffrey A.; Vittal, Jagadese J.

doi:10.1002/hc.520050315

Cited by 27 publications

(20 citation statements)

References 27 publications

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“…Again, addition across the Si–Ge double bond was observed in a regioselective manner to form Si–O and Ge–C bonds in compound 13 (Scheme ). This behavior is consistent with earlier studies by Baines and co-workers. − …”

Section: Resultssupporting

confidence: 93%

Basic Reactivity Pattern of a Cyclic Disilylated Germylene

et al. 2016

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In order to estimate the reactivity of disilylated germylene phosphine adducts, a cyclic version of this compound class was reacted with a number of different reagents. Reactions with the chalcogens sulfur, selenium, and tellurium led to dimers of the heavy ketone analogues. Reactions with water and ethyl bromide proceeded to give the respective oxidized germanol and germyl bromide. Two different reactions with alkynes were observed which led either to a germacyclopropene, by addition of tolane to the germylene, or to a silagermacyclobutene, likely formed by addition of the alkyne across a silagermene. Reaction via the silagermene was also observed in the reaction with benzophenone. Reaction of a germylene phosphine adduct with GeCl2·(dioxane) provided insertion of the silylated germylene into a Ge–Cl bond, leading to a germylated chlorogermylene phosphine adduct.

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Section: Resultssupporting

confidence: 93%

Basic Reactivity Pattern of a Cyclic Disilylated Germylene

et al. 2016

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“…In addition to the aforementioned linear systems, the chemistry of the cyclic trigermane (Mes 2 Ge) 3 has also been extensively investigated and it has been demonstrated that upon photolysis this species behaves as both a digermene and a germylene. [52][53][54][55][56][57][58][59][60][61][62][63][64][65][66] However, in contrast to the linear and cyclic oligogermanes the corresponding branched systems are relatively obscure. Prior to 2008, only a handful of these materials had been reported, including (Ph 3 Ge) 3 GeH, [72] (Ph 3 Ge) 3 GeMe, [72] (PhCl 2 Ge) 3 GePh, [73] (PhMe 2 Ge) 3 -GePh, [73] and (Ph(X) 2 Ge) 3 GePh (X = MeO, MeS, Me 2 N, Et 2 P).…”

Section: Introductionmentioning

confidence: 95%

“…Several different linear systems were prepared using the hydrogermolysis reaction and the combination of this process with a germanium hydride protection=deprotection strategy allowed the stepwise synthesis of linear systems where the germanium atoms are added to the chain one 56 C. S. WEINERT at a time. [6,8,[69][70][71] This is a powerful synthetic method, since it allows for variation of not only the length of the Ge -Ge backbone but also for the variation of the identity of the organic substituents attached to the GeGe chain.…”

Section: Introductionmentioning

confidence: 99%

Synthetic, Structural, and Physical Aspects of Organo-Oligogermanes

Weinert

2011

Comments on Inorganic Chemistry

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The hydrogermolysis reaction has been used to prepare a variety of linear and branched oligogermanes that have been fully characterized. The combination of a germanium hydride protection= deprotection strategy with the hydrogermolysis reaction allows for the addition of one or two germanium atoms to the Ge -Ge chain at a time in linear systems, or three germanium atoms at a time in the case of branched systems. The physical properties of both types of oligogermanes have been probed using UV=visible spectroscopy and cyclic voltammetry, and several of the experimental results have been complimented with theoretical investigations. The syntheses, structures, and properties of these oligogermanes are the foci of this review.

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“…disilenes, digermenes and distannenes) has been extensively investigated, 1 the chemistry of compounds containing a double bond between two different Group 14 elements beyond carbon was unknown until we reported the synthesis of tetramesitylgermasilene (Mes2Ge=SiMes2, Mes = 2,4,6-trimethylphenyl). 8 The most dramatic differences between Mes2Ge=SiMes2 and Mes2Si=SiMes2 are their relative stability and their decomposition pathways. 1 Mes2Ge=SiMes2 adds methanol 2 and water 4 across the central double bond, in a manner similar to the disilene and the digermene; however, in this case the regiochemistry of the addition becomes a factor in the reaction.…”

Section: Introductionmentioning

confidence: 99%

PHOTOCHEMICAL DISSOCIATION OF A GERMASILENE: PREPARATION AND PHOTOLYSIS OF Si, Si'-DI-TERT-BUTYL-TETRAMESITYLSILADIGERMIRANE

Kolleger¹,

Stibbs²,

Vittal³

et al. 1996

Main Group Metal Chemistry

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The preparation and photolysis (350 nm) of Si, Si'-di-terf-butyltetramesitylsiladigermirane, 1, has been investigated. The structure of the siladigermirane 1 has been determined by x-ray crystallography: crystals are monoclinic, space group C2/c with Ζ = 4 in a unit cell of dimensions a = 11.5830(9) A, b = 21.268(3) A, c = 17.534(2) A and β = 108.60(1)°. The structure was solved by direct methods and refined by full-matrix least squares on F 2 on the basis of 2361 observed reflections (Ι>2σ(Ι)) to R, and wR 2 values of 0.0495 and 0.0939, respectively. Photolysis of 1 in the presence of methanol gave two major products: MeSjGehKOMe) and i-Bu 2 Si(OMe)GeHMes 2 , 2 in a 1:1 ratio.Similarly, photolysis of 1 in the presence of water led to the isolation of f-Bi^SKOhOGeHMeSz, 3. The formation of compounds 2 and 3 is best explained by the regioselective photochemical cleavage of the siladigermirane to give MeSzGe: and /-Bu 2 Si=GeMes2, 4, followed by trapping of the germasilene, regioseledively, by water and methanol. Attempts to prepare a solution of germasilene 4 by photolysis of siladigermirane 1 in triethylsilane, a selective trapping reagent for MeSjGe:, were unsuccessful. The germasilene 4 undergoes photodissociation to yield another equivalent of Mes^e: and f-Bu 2 Si:, which were subsequently trapped by the silane.Brought to you by | Purdue University Libraries Authenticated Download Date | 5/27/15 7:32 PM

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The addition of carbonyl compounds to tetramesitylgermasilene and dimesitylgermylene

Cited by 27 publications

References 27 publications

Basic Reactivity Pattern of a Cyclic Disilylated Germylene

Basic Reactivity Pattern of a Cyclic Disilylated Germylene

Synthetic, Structural, and Physical Aspects of Organo-Oligogermanes

PHOTOCHEMICAL DISSOCIATION OF A GERMASILENE: PREPARATION AND PHOTOLYSIS OF Si, Si'-DI-TERT-BUTYL-TETRAMESITYLSILADIGERMIRANE

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