Synthesis and Characterization of a Novel Dialdehyde and Cyclic Anhydride

Wu, Liqiong; Li, Feng; Zhang, Hong; Liu, Qixuan; He, Xumin; Yang, Fang‐Zu; Xia, Haiping

doi:10.1021/jo800052u

Cited by 30 publications

(10 citation statements)

References 18 publications

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“…For example, it was recently reported by Xia and co-workers that treatment of the osmabenzene 11 with silver or copper acetylides led to the novel phosphonium substituted benzene derivatives 12, 13 or 14 (Scheme6). [113] Other organic molecules that have been obtained from metallabenzenep recursors include an unusual dialdehyde [114] and stable cyclopentadienyl ions. [90,92] In addition, metallabenzenes have been reported to have promising electrochemical, [51,56,90] optical [93,115] and cytotoxic properties.…”

Section: Metallabenzenesmentioning

confidence: 99%

Recent Advances in Metallaaromatic Chemistry

Frogley

Wright

2017

Chemistry A European J

141

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Metallaaromatics can be broadly defined as aromatic compounds in which one of the ring atoms is a transition metal. The metallabenzenes are one important class of these compounds that has undergone extensive study recently. Closely related species such as fused-ring metallabenzenes, heterometallabenzenes, π-coordinated metallabenzenes and metallabenzynes have also attracted considerable attention. Although many metallaaromatics can be considered as metalla-analogues of classic organic aromatic compounds, this is not always the case. Recent seminal studies have shown that metallapentalenes and metallapentalynes, which are metalla-analogues of the anti-aromatic compounds pentalene and pentalyne, are in fact aromatic and highly stable. Very unusual spiro-metallaaromatic compounds have also recently been isolated. In this concepts article, key features of all these intriguing metallaaromatic compounds are discussed with reference to the structural, spectroscopic, reactivity and theoretical studies that have been undertaken. These compounds continue to generate much interest, not only because of the contributions they make to fundamental chemical understanding, but also because of the promise of possible practical applications.

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Section: Metallabenzenesmentioning

confidence: 99%

Recent Advances in Metallaaromatic Chemistry

Frogley

Wright

2017

Chemistry A European J

141

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“…161,162 The 1,3dicarbonyls are commonly employed as feedstocks to construct pyrazoles by condensation with a aryl or alkyl hydrazine, while their low stability restricts their applicability for obtaining substituted pyrazoles. 163,164 On the other hand, 1,3-diacetals or vinylogous formamides 37 by reaction with hydrazines 38 allow access to substituted pyrazole motifs 39 (path A, Scheme 13), while multistep synthesis procedures were prerequisite due to the existence of sensitive functional groups. 165 Much attention has been paid to the development of more efficient routes for substituted pyrazoles.…”

Section: Pyrazolesmentioning

confidence: 99%

Cycloamination strategies for renewable N-heterocycles

et al. 2020

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“…The metal–carbon bond of osmanaphthalene could be oxidized in the presence of oxygen to generate an osmanaphthalyne with metal–carbon triple bond . As shown in Scheme , treatment of ruthenabenzene 4 with nitric acid, followed by the addition of NaHCO 3 , led to the cleavage of the two ruthenium–carbon bonds to produce an unusual dialdehyde containing two phosphonium groups ( 32 ) …”

Section: Reactions With Electrophilesmentioning

confidence: 99%

“…[30] As shown in Scheme 14, treatment of ruthenabenzene 4 with nitric acid, followed by the addition of NaHCO 3 ,l ed to the cleavage of the two ruthenium-carbon bonds to produce an unusualdialdehyde containing two phosphonium groups (32). [31] Scheme10. Reactionofi ridabenzene 23 with MeCN.…”

Section: Reactions With Electrophilesmentioning

confidence: 99%

Reactions of Metal–Carbon Bonds within Six‐Membered Metallaaromatic Rings

Zhou

Zhang

2018

Chemistry A European J

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Metallaaromatics represent a distinct and attractive class of heterocycles, which have greatly expanded the library of known aromatics. They have garnered extensive research interest on account of their unique properties, organometallic reactivity, and aromaticity. The metal-carbon bonds have been regarded as the most active reaction sites of metallaaromatics and a variety of related reactions have been demonstrated in the literature. This Minireview summarized recent findings on the reactivity of the metal-carbon bonds, mainly relevant to the representative metallaaromatics with six-membered ring scaffolds. A series of reactions occurred on the metal-carbon bonds, including the nucleophilic addition reactions, nucleophilic aromatic substitution reactions, electrophilic addition reactions, reactions with unsaturated compounds, and migratory insertion reactions, have been classified. These reactions demonstrate that the metal-carbon bonds of metallaaromatics can undergo typical reactions for both aromatic species and metal carbene/carbyne complexes. Meanwhile, the reactivity trends of the metal-carbon bonds are strongly affected by the metal centers and the effect of the corresponding substituents of metallacycles.

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Synthesis and Characterization of a Novel Dialdehyde and Cyclic Anhydride

Cited by 30 publications

References 18 publications

Recent Advances in Metallaaromatic Chemistry

Recent Advances in Metallaaromatic Chemistry

Cycloamination strategies for renewable N-heterocycles

Reactions of Metal–Carbon Bonds within Six‐Membered Metallaaromatic Rings

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