Reactions of Mesityl Azide with Ferrocene-Based N-Heterocyclic Germylenes, Stannylenes and Plumbylenes, Including PPh 2 -Functionalised Congeners
The reactivity of ferrocene-based N-heterocyclic tetrylenes [{Fe(η -C H -NSitBuMe ) }E] (E=Ge, Sn, Pb) towards mesityl azide (MesN ) is compared with that of PPh -functionalised congeners exhibiting two possible reaction sites, namely the E and P atom. For E=Ge and Sn the reaction occurs at the E at...
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| Published in | Chemistry : a European journal Vol. 28; no. 42; p. e202200996 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
26.07.2022
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| Subjects | |
| Online Access | Get full text |
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| Abstract | The reactivity of ferrocene-based N-heterocyclic tetrylenes [{Fe(η
-C
H
-NSitBuMe
)
}E] (E=Ge, Sn, Pb) towards mesityl azide (MesN
) is compared with that of PPh
-functionalised congeners exhibiting two possible reaction sites, namely the E
and P
atom. For E=Ge and Sn the reaction occurs at the E
atom, leading to the formation of N
and an E
=NMes unit. The germanimines are sufficiently stable for isolation. The stannanimines furnish follow-up products, either by [2+3] cycloaddition with MesN
or, in the PPh
-substituted case, by NMes transfer from the Sn
to the P
atom. Whereas [{Fe(η
-C
H
-NSitBuMe
)
}Pb] and other diaminoplumbylenes studied are inert even under forcing conditions, the PPh
-substituted congener forms an addition product with MesN
, thus showing a behaviour similar to that of frustrated Lewis pairs. The germylenes of this study afford copper(I) complexes with CuCl, including the first structurally characterised linear dicoordinate halogenido complex [CuX(L)] with a heavier tetrylene ligand L. |
|---|---|
| AbstractList | The reactivity of ferrocene-based N-heterocyclic tetrylenes [{Fe(η
-C
H
-NSitBuMe
)
}E] (E=Ge, Sn, Pb) towards mesityl azide (MesN
) is compared with that of PPh
-functionalised congeners exhibiting two possible reaction sites, namely the E
and P
atom. For E=Ge and Sn the reaction occurs at the E
atom, leading to the formation of N
and an E
=NMes unit. The germanimines are sufficiently stable for isolation. The stannanimines furnish follow-up products, either by [2+3] cycloaddition with MesN
or, in the PPh
-substituted case, by NMes transfer from the Sn
to the P
atom. Whereas [{Fe(η
-C
H
-NSitBuMe
)
}Pb] and other diaminoplumbylenes studied are inert even under forcing conditions, the PPh
-substituted congener forms an addition product with MesN
, thus showing a behaviour similar to that of frustrated Lewis pairs. The germylenes of this study afford copper(I) complexes with CuCl, including the first structurally characterised linear dicoordinate halogenido complex [CuX(L)] with a heavier tetrylene ligand L. Abstract The reactivity of ferrocene‐based N‐heterocyclic tetrylenes [{Fe(η 5 −C 5 H 4 −NSi t BuMe 2 ) 2 }E] (E=Ge, Sn, Pb) towards mesityl azide (MesN 3 ) is compared with that of PPh 2 ‐functionalised congeners exhibiting two possible reaction sites, namely the E II and P III atom. For E=Ge and Sn the reaction occurs at the E II atom, leading to the formation of N 2 and an E IV =NMes unit. The germanimines are sufficiently stable for isolation. The stannanimines furnish follow‐up products, either by [2+3] cycloaddition with MesN 3 or, in the PPh 2 ‐substituted case, by NMes transfer from the Sn IV to the P III atom. Whereas [{Fe(η 5 −C 5 H 4 −NSi t BuMe 2 ) 2 }Pb] and other diaminoplumbylenes studied are inert even under forcing conditions, the PPh 2 ‐substituted congener forms an addition product with MesN 3 , thus showing a behaviour similar to that of frustrated Lewis pairs. The germylenes of this study afford copper(I) complexes with CuCl, including the first structurally characterised linear dicoordinate halogenido complex [CuX(L)] with a heavier tetrylene ligand L. |
| Author | Siemeling, Ulrich Bruhn, Clemens Guthardt, Robin Oetzel, Lisa Lang, Tobias |
| Author_xml | – sequence: 1 givenname: Robin orcidid: 0000-0002-7694-1654 surname: Guthardt fullname: Guthardt, Robin organization: Present address: School of Chemistry, Monash University, PO Box 23, VIC 3800, Melbourne, Australia – sequence: 2 givenname: Lisa surname: Oetzel fullname: Oetzel, Lisa organization: Institute of Chemistry, University of Kassel, Heinrich-Plett-Straße 40, 34132, Kassel, Germany – sequence: 3 givenname: Tobias surname: Lang fullname: Lang, Tobias organization: Institute of Chemistry, University of Kassel, Heinrich-Plett-Straße 40, 34132, Kassel, Germany – sequence: 4 givenname: Clemens surname: Bruhn fullname: Bruhn, Clemens organization: Institute of Chemistry, University of Kassel, Heinrich-Plett-Straße 40, 34132, Kassel, Germany – sequence: 5 givenname: Ulrich orcidid: 0000-0002-8617-7768 surname: Siemeling fullname: Siemeling, Ulrich organization: Institute of Chemistry, University of Kassel, Heinrich-Plett-Straße 40, 34132, Kassel, Germany |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/35510599$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1039_D3CS00290J crossref_primary_10_1002_asia_202300634 crossref_primary_10_1021_acs_organomet_3c00318 crossref_primary_10_1039_D2CC05970C crossref_primary_10_1039_D3DT02684A crossref_primary_10_3390_ijms241210218 crossref_primary_10_1021_acs_inorgchem_3c03353 |
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| Keywords | tetrylenes Azides carbene homologues subvalent compounds metallocenes |
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| Snippet | The reactivity of ferrocene-based N-heterocyclic tetrylenes [{Fe(η
-C
H
-NSitBuMe
)
}E] (E=Ge, Sn, Pb) towards mesityl azide (MesN
) is compared with that of... Abstract The reactivity of ferrocene‐based N‐heterocyclic tetrylenes [{Fe(η 5 −C 5 H 4 −NSi t BuMe 2 ) 2 }E] (E=Ge, Sn, Pb) towards mesityl azide (MesN 3 ) is... |
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| SourceType | Aggregation Database Index Database |
| StartPage | e202200996 |
| SubjectTerms | Azides Coordination Complexes Lead Metallocenes Models, Molecular |
| Title | Reactions of Mesityl Azide with Ferrocene-Based N-Heterocyclic Germylenes, Stannylenes and Plumbylenes, Including PPh 2 -Functionalised Congeners |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/35510599 |
| Volume | 28 |
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