Reaktionen von komplexliganden

Dötz, Karl Heinz; Sturm, Werner

doi:10.1016/s0022-328x(00)99559-7

Cited by 9 publications

(8 citation statements)

References 7 publications

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“…The value in the solid is rather low compared to the reported range for cyclobutenones (solid: 1757–1760 cm –1 solid. CDCl 3 : 1753–1758 cm –1 ) . Two intramolecular short CH ··· O distances of 2.90 and 2.81 Å, namely from the 2‐ferrocenyl (α‐CH) and 4‐ferrocenyl (unsubstituted Cp‐H) substituent, might be responsible for this finding especially in the solid state.…”

Section: Resultsmentioning

confidence: 90%

“…In a formal retrosynthesis, the triferrocenyl cyclobutenone derivative 3 can be derived from a CO unit and three ferrocenyl carbenes (under partial desalkoxylation). As cyclobutenones are accessible from alkynes and Fischer carbene complexes (lacking conjugated aryl or vinyl carbene substituents which would enable the Dötz reaction, Scheme a) according to previous work by Zora and co‐workers (Scheme a), the formation of 3 from 1 might be traced back to a thermally induced formation of the required diferrocenyl alkyne Fc–C≡C–Fc …”

Section: Resultsmentioning

confidence: 99%

“…CDCl 3 : 1753-1758 cm -1 ). [14][15][16][17][18] Two intramolecular short CH•••O distances of 2.90 and 2.81 Å, namely from the 2-ferrocenyl (α-CH) and 4-ferrocenyl (unsubstituted Cp-H) substituent, might be responsible for this finding especially in the solid state. According to quantum chemical calculations, these CH stretches indeed couple to the carbonyl stretching vibration ( Figure S15, Supporting Information).…”

Section: Synthesis and Characterization Ofmentioning

confidence: 94%

“…For example, treating vinyl or aryl‐substituted alkoxy carbenes with alkynes yields phenols and naphthols, respectively (Scheme a, Dötz benzannulation reaction) . Carbenes with 1,3‐difluorphenyl‐, cyclopropyl or ferrocenyl substituents furnish cyclobutenones (or cyclopentenones) in the presence of alkynes (Scheme a, Zora) …”

Section: Introductionmentioning

confidence: 99%

“…[7][8][9][10][11][12][13] Carbenes with 1,3-difluorphenyl-, cyclopropyl or ferrocenyl substituents furnish cyclobutenones (or cyclopentenones) in the presence of alkynes (Scheme 1a, Zora). [14][15][16][17][18][19][20][21] In these cases, the initial steps comprise CO dissociation from the carbene complex. Hence, thermal activation is typically required.…”

Section: Introductionmentioning

confidence: 99%

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Unexpected C–C Bond Formation with a Ferrocenyl Fischer Carbene Complex

Veit

Seibert

Förster

et al. 2020

Zeitschrift anorg allge chemie

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Thermolysis of (OC)5Cr(C(OEt)(Fc)) (1) gives 2,N‐diferrocenyl acetamide Fc–CH2–CO–NH–Fc (2) in the presence of amino ferrocene Fc‐NH2. In the absence of a nucleophile, 4‐ethoxy‐2,3,4‐triferrocenyl‐cyclobut‐2‐enone (3) forms from 1 under thermal activation. Single crystal X‐ray diffraction, NMR spectroscopy and mass spectrometry unambiguously confirm the structure of both unexpected products. Quantum chemical calculations and kinetic experiments by mass spectrometry and IR spectroscopy help to propose conceivable pathways to their formation.

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Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: Synthesis and Characterization Ofmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Unexpected C–C Bond Formation with a Ferrocenyl Fischer Carbene Complex

Veit

Seibert

Förster

et al. 2020

Zeitschrift anorg allge chemie

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The Synthesis of Phenols and Quinones viaFischer Carbene Complexes

Waters

Wulff

2008

Organic Reactions

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Fischer carbene complexes can be broadly defined as those transition‐metal carbene complexes that have a low oxidation state, have an electrophilic carbene carbon , and usually have a heteroatom‐stabilizing substituent on the carbene carbon. Fischer complexes were the first examples of any type of transition metal carbene complexes to be reported. The reaction of Fischer carbene complexes with alkynes is facile, occurring just above ambient temperature, and resulting in the assembly of a benzene ring from the three carbons of the alpha, beta‐unsaturated carbine complex, the two carbons of the alkyne, and the carbon of a carbon monoxide ligand. The synthetic value of this reaction stems from its broad scope, the generally high yields for the process, and the fact that that the products can function as intermediates for the synthesis of a variety of aromatic compounds including para ‐quinones. It is the most synthetically valuable of the large number of Fischer carbene complexes that have been developed for applications in synthetic organic chemistry. This chapter is the first comprehensive review that is limited to the synthesis of phenols and quinones from the reactions of Fischer carbene complexes with alkynes.

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