A silylene-stabilized distannavinylidene with a highly labile substituent

Qiao, Zihao; Chen, Ming; Mo, Zhenbo

doi:10.1007/s11426-023-1855-y

Sci. China Chem.

2023

DOI: 10.1007/s11426-023-1855-y

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A silylene-stabilized distannavinylidene with a highly labile substituent

Zihao Qiao,

Ming Chen,

Zhenbo Mo

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2024

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Cited by 3 publications

References 55 publications

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Double 1,2‐Carbon Migration at Mixed Heavier Sn=Ge Vinylidenes

Qiao,

Li,

Chen

et al. 2024

Angewandte Chemie

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1,2‐migration is one recurring isomerization reaction in organic chemistry. In contrast, double 1,2‐migration remains rare and limited to transition‐metal complexes. Herein, we describe the synthesis, characterization and reactivity of mixed heavier Sn=Ge vinylidenes. Double 1,2‐carbon migration enables the isomerization of the stannagermenylidene (3) to the germastannenylidene (4). X‐ray diffraction analysis and DFT calculations revealed that 3 and 4 feature a Sn=Ge double bond. The reaction of 3 with IMe2 (1,3,4,5‐tetramethylimidazoline‐2‐ylidene) results in the electron redistribution in the Sn=Ge core to give the germylone‐stannylene adduct (5). Moreover, treatment of 3 with 0.25 equiv. of (AlCp*)4 produces the heteronuclear aluminyl stannagermyne (6).

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Double 1,2‐Carbon Migration at Mixed Heavier Sn=Ge Vinylidenes

Qiao,

Li,

Chen

et al. 2024

Angewandte Chemie

Self Cite

View full text Add to dashboard Cite

show abstract

Double 1,2‐Carbon Migration at Mixed Heavier Sn=Ge Vinylidenes

Qiao,

Li,

Chen

et al. 2024

Angew Chem Int Ed

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Isolation of a NHC-stabilized heavier nitrile and its conversion into an isonitrile analogue

Doleschal,

Kostenko,

Liu

et al. 2024

Nat. Chem.

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Nitriles (R–C≡N) have been investigated since the late eighteenth century and are ubiquitous encounters in organic and inorganic syntheses. In contrast, heavier nitriles, which contain the heavier analogues of carbon and nitrogen, are sparsely investigated species. Here we report the synthesis and isolation of a phosphino-silylene featuring an N-heterocyclic carbene-phosphinidene and a highly sterically demanding silyl group as substituents. Due to its unique structural motif, it can be regarded as a Lewis base-stabilized heavier nitrile. The Si–P bond displays multiple bond character and a bent R–Si–P geometry, the latter indicating fundamental differences between heavier and classical nitriles. In solution, a quantitative unusual rearrangement to a phosphasilenylidene occurs. This rearrangement is consistent with theoretical predictions of rearrangements from heavier nitriles to heavier isonitriles. Our preliminary reactivity studies revealed that both isomers exhibit highly nucleophilic silicon centres capable of oxidative addition and coordination to iron tetracarbonyl.

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A silylene-stabilized distannavinylidene with a highly labile substituent

Cited by 3 publications

References 55 publications

Double 1,2‐Carbon Migration at Mixed Heavier Sn=Ge Vinylidenes

Double 1,2‐Carbon Migration at Mixed Heavier Sn=Ge Vinylidenes

Double 1,2‐Carbon Migration at Mixed Heavier Sn=Ge Vinylidenes

Isolation of a NHC-stabilized heavier nitrile and its conversion into an isonitrile analogue

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