Chromium Complexes Containing Polycyclic Condensed Aromatic Ligands: Mono- and Bidirectional Synthesis from Chromium-Carbenes, Molecular Structures, and Rearrangement Reactions
Chromium–pyrenylcarbenes accessible from halopyrene precursors undergo benzannulation upon gentle warming with 3‐hexyne to give hydroquinoid benzopyrene–Cr(CO)3 complexes. Kinetic benzannulation product 3 rearranges into thermodynamic haptotropomer 4 at 70 °C in octafluorotoluene under first‐order k...
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| Published in | European journal of inorganic chemistry Vol. 2014; no. 9; pp. 1462 - 1469 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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WILEY-VCH Verlag
01.03.2014
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| Abstract | Chromium–pyrenylcarbenes accessible from halopyrene precursors undergo benzannulation upon gentle warming with 3‐hexyne to give hydroquinoid benzopyrene–Cr(CO)3 complexes. Kinetic benzannulation product 3 rearranges into thermodynamic haptotropomer 4 at 70 °C in octafluorotoluene under first‐order kinetics. Further complexation of 3 by Cr(NH3)3(CO)3 affords syn and anti dinuclear chromium–benzopyrene complexes. Bidirectional extension of the benzannulation protocol results in the formation of syn and anti dibenzopyrene–dichromium complexes, which are structurally characterized by X‐ray analysis.
A benzannulation/metal migration sequence allows the thermocontrolled regioselective transformation of pyrenylcarbene–chromium into hydroquinoid benzopyrene–chromium complexes. Bidirectional extension of the protocol to a 1,8‐pyrenediylbis(carbene) complex affords syn‐ and anti‐dinuclear dibenzopyrene–Cr(CO)3 complexes. TBDMS = tert‐butyldimethylsilyl, Tf = trifluoromethylsulfonyl. |
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| AbstractList | Chromium-pyrenylcarbenes accessible from halopyrene precursors undergo benzannulation upon gentle warming with 3-hexyne to give hydroquinoid benzopyrene-Cr(CO) sub(3) complexes. Kinetic benzannulation product 3 rearranges into thermodynamic haptotropomer 4 at 70 degree C in octafluorotoluene under first-order kinetics. Further complexation of 3 by Cr(NH sub(3)) sub(3)(CO) sub(3) affords syn and anti dinuclear chromium-benzopyrene complexes. Bidirectional extension of the benzannulation protocol results in the formation of syn and anti dibenzopyrene-dichromium complexes, which are structurally characterized by X-ray analysis. A benzannulation/metal migration sequence allows the thermocontrolled regioselective transformation of pyrenylcarbene-chromium into hydroquinoid benzopyrene-chromium complexes. Bidirectional extension of the protocol to a 1,8-pyrenediylbis(carbene) complex affords syn- and anti-dinuclear dibenzopyrene-Cr(CO) sub(3) complexes. TBDMS = tert-butyldimethylsilyl, Tf = trifluoromethylsulfonyl. Abstract Chromium–pyrenylcarbenes accessible from halopyrene precursors undergo benzannulation upon gentle warming with 3‐hexyne to give hydroquinoid benzopyrene–Cr(CO) 3 complexes. Kinetic benzannulation product 3 rearranges into thermodynamic haptotropomer 4 at 70 °C in octafluorotoluene under first‐order kinetics. Further complexation of 3 by Cr(NH 3 ) 3 (CO) 3 affords syn and anti dinuclear chromium–benzopyrene complexes. Bidirectional extension of the benzannulation protocol results in the formation of syn and anti dibenzopyrene–dichromium complexes, which are structurally characterized by X‐ray analysis. Chromium–pyrenylcarbenes accessible from halopyrene precursors undergo benzannulation upon gentle warming with 3‐hexyne to give hydroquinoid benzopyrene–Cr(CO)3 complexes. Kinetic benzannulation product 3 rearranges into thermodynamic haptotropomer 4 at 70 °C in octafluorotoluene under first‐order kinetics. Further complexation of 3 by Cr(NH3)3(CO)3 affords syn and anti dinuclear chromium–benzopyrene complexes. Bidirectional extension of the benzannulation protocol results in the formation of syn and anti dibenzopyrene–dichromium complexes, which are structurally characterized by X‐ray analysis. A benzannulation/metal migration sequence allows the thermocontrolled regioselective transformation of pyrenylcarbene–chromium into hydroquinoid benzopyrene–chromium complexes. Bidirectional extension of the protocol to a 1,8‐pyrenediylbis(carbene) complex affords syn‐ and anti‐dinuclear dibenzopyrene–Cr(CO)3 complexes. TBDMS = tert‐butyldimethylsilyl, Tf = trifluoromethylsulfonyl. Chromium-pyrenylcarbenes accessible from halopyrene precursors undergo benzannulation upon gentle warming with 3-hexyne to give hydroquinoid benzopyrene-Cr(CO)3 complexes. Kinetic benzannulation product 3 rearranges into thermodynamic haptotropomer 4 at 70 °C in octafluorotoluene under first-order kinetics. Further complexation of 3 by Cr(NH3)3(CO)3 affords syn and anti dinuclear chromium-benzopyrene complexes. Bidirectional extension of the benzannulation protocol results in the formation of syn and anti dibenzopyrene-dichromium complexes, which are structurally characterized by X-ray analysis. [PUBLICATION ABSTRACT] |
| Author | Hegele, Peter Daniels, Jörg Dötz, Karl Heinz Schnakenburg, Gregor |
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| CitedBy_id | crossref_primary_10_1039_D0DT00323A crossref_primary_10_1016_j_ccr_2015_09_012 crossref_primary_10_1016_j_ccr_2022_214575 crossref_primary_10_1016_j_tet_2016_03_047 crossref_primary_10_1039_C4DT02736A |
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| Snippet | Chromium–pyrenylcarbenes accessible from halopyrene precursors undergo benzannulation upon gentle warming with 3‐hexyne to give hydroquinoid... Abstract Chromium–pyrenylcarbenes accessible from halopyrene precursors undergo benzannulation upon gentle warming with 3‐hexyne to give hydroquinoid... Chromium-pyrenylcarbenes accessible from halopyrene precursors undergo benzannulation upon gentle warming with 3-hexyne to give hydroquinoid... Chromium-pyrenylcarbenes accessible from halopyrene precursors undergo benzannulation upon gentle warming with 3-hexyne to give hydroquinoid benzopyrene-Cr(CO)... |
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| SubjectTerms | Accessibility Arene ligands Benzannulation Bidirectional Carbenes Chromium Complexation Ligands Metal migration Migration Precursors Reaction kinetics Transformations |
| Title | Chromium Complexes Containing Polycyclic Condensed Aromatic Ligands: Mono- and Bidirectional Synthesis from Chromium-Carbenes, Molecular Structures, and Rearrangement Reactions |
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