Synthesis and Characterization of Dirhenadehydro[12]annulenes

Chen, Jiangxi; Lee, Ka‐Ho; Sung, Herman H. Y.; Williams, Ian D.; Lin, Zhenyang; Jia, Guochen

doi:10.1002/anie.201601562

Cited by 24 publications

(17 citation statements)

References 76 publications

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“…The identities of complexes 14 have been confirmed by X‐ray diffraction studies and are supported by their spectroscopic data. We have reported in our preliminary report that the solid‐state structure of 14 a contains an essentially planar twelve‐membered metallacycle. We now found that the complex 14 b has structural features like those of 14 a , as shown in Figure .…”

Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

“…In our preliminary communication, we reported that the methyl rhenium carbynes 13 containing a terminal alkynyl group can eliminate methane to give the dirhenadehydro[12]annulenes 14 via a σ-bond metathesis mechanism (Scheme 1). [16] The reported synthetic procedure in the communication is not efficient and involves three steps starting from the carbyne complexes 16. We have therefore searched for alternative routes to the complexes.…”

Section: Synthesis Of Dirhenadehydro[12]annulenesmentioning

confidence: 99%

“…The dirhenadehydro[12]annulenes are interesting, because their organic counterparts, are important members of antiaromatic annulenes and can be used as building blocks to construct organogels or supramolecular nanofibers . A preliminary report on this work has been published previously …”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Electronic Structure of Dirhenadehyro[12]annulene Complexes

et al. 2018

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Treatment of the SiMe3‐protected dichloro‐rhenium carbyne complexes Re{≡CCH=C(R)C≡CSiMe3}Cl2(PMe2Ph)3 (R = CMe3, 1‐adamantyl) with CsF in methanol directly afforded the 12‐membered metallacycles {ReCl(PMe2Ph)3}2{≡CCH=C(R)C≡C−}2. The electronic structure of the metallacycle was investigated by density functional calculations. The UV‐vis spectrum of the metallacycle shows a red‐shifted band compared to that of the starting dichlorocarbyne complex. Treatment of {ReCl(PMe2Ph)3}2{≡CCH=C(CMe3)C≡C−}2 with HCl produced the dichloro‐rhenium carbyne complex Re{≡CCH=C(CMe3)C≡CH}Cl2(PMe2Ph)3, which is consistent with the electronic structure of the 12‐membered metallacycles.

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Dirhenadehydro[12]annulenesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Electronic Structure of Dirhenadehyro[12]annulene Complexes

et al. 2018

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“…Reported metallacycles includem etallabenzenes, [1,2] metallabenzynes, [3,4] metallaannulenes, [5] and other metallacycles. Reported metallacycles includem etallabenzenes, [1,2] metallabenzynes, [3,4] metallaannulenes, [5] and other metallacycles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Photothermal Osmium Carbolong Complexes

Qin

Lin

et al. 2018

Chemistry A European J

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Metallacycles with chelating polydentate conjugated-carbon chain ligands are called carbolong complexes, which are expected to have interesting properties. In this work, the preparation of 12-carbon carbolong complexes in which all of the coordinated atoms in the equatorial plane are carbon atoms was studied. With the help of the well-established mechanism, a new approach to prepare coplanar carbolong complexes bearing different organic functional groups was developed by adding different terminal alkynes in sequence. In the presence of HBF , these coplanar carbolong complexes were converted to η -allyl osmapentalene derivatives, which can be produced directly from the reaction of cyclopropaosmapentalene 1 with terminal alkynes in the presence of AgBF under anhydrous conditions. This study offers a new route for the preparation of functional osmium carbolong complexes with excellent photothermal properties, which can be used to prepare photothermal materials.

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Craig‐Hückel Hybrid Aromatic Metalla‐dehydro[11]annulenes Constructed by a Formal [10+1] Cycloaddition Reaction

Ruan,

Lu,

Rao

et al. 2024

Angewandte Chemie

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Aromatic metalla‐annulenes are important aromatic compounds, research into which has been mainly concentrated on metal‐benzenes and their lower homologues. Reports on their superior homologs are rare, and this has greatly limited the systematic study of their properties. In this work, a series of osma‐dehydro[11]annulenes with good air and thermal stability were prepared in high yields through a simple [10+1] strategy, by incorporating a metal fragment into conjugated ten‐carbon chains in a one‐pot reaction. They are the first monometallic aromatic metalla‐[n]annulenes with the ring size larger than 6, and their Craig‐Hückel hybrid aromaticity is supported by various physical and computational parameters. Besides, these complexes show versatile reactivities, not only giving further evidence for their aromaticity, but also demonstrating their physical and chemical properties can easily be regulated. This work enriches the metalla‐aromatic chemistry, and provides a new avenue for the synthesis of large metalla‐annulenes with different ring sizes.

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Synthesis and Characterization of Dirhenadehydro[12]annulenes

Cited by 24 publications

References 76 publications

Synthesis, Characterization and Electronic Structure of Dirhenadehyro[12]annulene Complexes

Synthesis, Characterization and Electronic Structure of Dirhenadehyro[12]annulene Complexes

Synthesis and Characterization of Photothermal Osmium Carbolong Complexes

Craig‐Hückel Hybrid Aromatic Metalla‐dehydro[11]annulenes Constructed by a Formal [10+1] Cycloaddition Reaction

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