The Novel, [n‐B20H18]2−‐Induced Nucleophilic Ring Opening of Tetrahydrofuran by Alkoxide Anions

Li, Fangbiao; Shelly, Kenneth; Kane, Robert R.; Knobler, Carolyn B.; Hawthorne, M. Frederick

doi:10.1002/anie.199626461

Cited by 22 publications

(36 citation statements)

References 14 publications

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“…Therefore a slurry of (1) into an aqueous sodium hydroxide solution was stirred overnight. As expected from the results obtained with other clusters [12][13][14][15][16], a ring-opening reaction has occurred (Scheme 2).…”

Section: Ring-opening Reaction Synthesis Of [P(c 6 H 5 ) 4 ] 2 [2-b supporting

confidence: 71%

Synthesis and X-ray structural characterisation of the tetramethylene oxonium derivative of the hydrodecaborate anion. A versatile route for derivative chemistry of [B10H10]2−

Bernard

Cornu

Perrin

et al. 2004

Journal of Organometallic Chemistry

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Section: Ring-opening Reaction Synthesis Of [P(c 6 H 5 ) 4 ] 2 [2-b supporting

confidence: 71%

Synthesis and X-ray structural characterisation of the tetramethylene oxonium derivative of the hydrodecaborate anion. A versatile route for derivative chemistry of [B10H10]2−

Bernard

Cornu

Perrin

et al. 2004

Journal of Organometallic Chemistry

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“…A third isomer of 1, cis-1, was recently produced 21 from the low temperature (0 °C) oxidation of [ae-B 20 H 18 ] 42 with Fe 3+ (vide infra). As in trans-1, the two [B 10 H 9 ] 2 cages of cis-1 are connected by a pair of three-center two-electron B-B-B bonds, but using different boron vertices such that the [B 10 H 9 ] 2 components are nonequivalent and arranged in a cisoid configuration (Scheme 2).…”

Section: Isomers Of [B 20 H 18 ] 22 (1)mentioning

confidence: 99%

The versatile chemistry of the [B20H18]2– ions: novel reactions and structural motifs

Hawthorne

Shelly

2002

Chem. Commun.

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Among the polyhedral [closo-BnHn]2- ion series (n = 5-12 inclusive) the aromatic [closo-B10H10]2- ion is both readily available and quite reactive. Among its many reactions which retain its cage structure one finds the oxidative dimerization reaction in which two [closo-B10H12]2- ions each formally lose a hydride ion and undergo dimerization of the resulting [closo-B10H9]- ions to produce the [trans-B20H18]2- ion. The two-component [closo-B10H9]- ions of the latter are linked together by a pair of unique B-B-B bonds which provide unprecedented reactivity to the structure. Among these reactions are the two-electron reduction to a set of three interconvertible [B20H18]4- ions having intercage B-B bonds and the related reductive substitution reaction in which [trans-B20H18]2- undergoes attack by nucleophile, L, to produce [B20H18L]2-. The latter species is formally a substituted [B20H19]3- (L = H) ion formed by B-B bond protonation of one of the isomeric [B20H18]4- ions. These and a variety of novel reactions are described here along with interrelated reaction mechanisms considered for the first time.

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“…This conclusion is in agreement with the experimental facts that the dianion can be reduced to tetraanion with sodium in liquid ammonia solution. 6 The Figure 2c …”

Section: On Electron-counting Rulementioning

confidence: 98%

“…The species (1), (2), (4), (5), and (6) have been characterized by experiments. 6,13 The species (3) and (7) represent two new boranes that are considered in this paper for the first time. The optimized bond lengths are listed in Table1.…”

Section: Optimized Geometries and Stabilitymentioning

confidence: 99%

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Ab initio studies on isomers of macropolyhedral borane ions [B₂₀H₁₈]ⁿ (n = 0, –2, –4)

Zhang

Zhao

et al. 2006

J Comput Chem

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Various isomers of macropolyhedral borane ions [B20H18]n (n = 0, -2, -4) are investigated by using the density functional theory methods at RB3LYP/6-31+G* and RB3LYP/6-31G* levels to obtain the optimized geometries, harmonic vibrational frequencies, electron structures, and the stability order. The calculated results show that optimized bond lengths are consistent with the available experimental values and the natural populations, taking [a2 -B20H18]4- (4) as an example, are also in agreement with NMR spectra. The calculated vibrational frequencies are all real, so all of these isomers could be stable, among which [a2 -B20H18]2- (3) and [a2 -B20H18]0 (7) are considered for the first time in this paper. On the basis of the contour maps of molecular orbitals, the delocalized characteristic of molecular orbitals and the possible redox mechanism of these ions are also discussed. Moreover, the analysis on counting of skeletal bonding electrons shows that the isomers (1)-(6) obey the electronic requirement predicted by the mno rule, whereas the newly predicted isomer (7) does not match the mno rule.

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The Novel, [n‐B₂₀H₁₈]²⁻‐Induced Nucleophilic Ring Opening of Tetrahydrofuran by Alkoxide Anions

Cited by 22 publications

References 14 publications

Synthesis and X-ray structural characterisation of the tetramethylene oxonium derivative of the hydrodecaborate anion. A versatile route for derivative chemistry of [B10H10]2−

Synthesis and X-ray structural characterisation of the tetramethylene oxonium derivative of the hydrodecaborate anion. A versatile route for derivative chemistry of [B10H10]2−

The versatile chemistry of the [B20H18]2– ions: novel reactions and structural motifs

Ab initio studies on isomers of macropolyhedral borane ions [B₂₀H₁₈]ⁿ (n = 0, –2, –4)

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The Novel, [n‐B20H18]2−‐Induced Nucleophilic Ring Opening of Tetrahydrofuran by Alkoxide Anions

Cited by 22 publications

References 14 publications

Synthesis and X-ray structural characterisation of the tetramethylene oxonium derivative of the hydrodecaborate anion. A versatile route for derivative chemistry of [B10H10]2−

Synthesis and X-ray structural characterisation of the tetramethylene oxonium derivative of the hydrodecaborate anion. A versatile route for derivative chemistry of [B10H10]2−

The versatile chemistry of the [B20H18]2– ions: novel reactions and structural motifs

Ab initio studies on isomers of macropolyhedral borane ions [B20H18]n (n = 0, –2, –4)

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Product

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The Novel, [n‐B₂₀H₁₈]²⁻‐Induced Nucleophilic Ring Opening of Tetrahydrofuran by Alkoxide Anions

Ab initio studies on isomers of macropolyhedral borane ions [B₂₀H₁₈]ⁿ (n = 0, –2, –4)