Insertion of isocyanide and carbon monoxide into α,ω- octadiendiylnickel and an allene derived bis-π-allylnickel complex

Baker, Raymond; COPELAND, A. H.

doi:10.1016/0040-4039(76)80163-3

Cited by 14 publications

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“…Spectroscopic evidence for a bis(allyl)nickel carbonyl complex was obtained when Baker treated the bridged nickel allyl complex derived from 2,3,5-tris(methylene)hexamethylene with CO at −78 °C; the resulting red solution displayed a strong IR resonance at 2000 cm −1 . 9 Warming the reaction mixture to −30 °C in the presence of additional CO caused the signal to disappear, however, and the cyclic insertion product 3,4,6-trimethylenecycloheptanone was identified (eq 3). The unisolated, thermally unstable species 1 was proposed as the source of the transient IR resonance.…”

Section: ■ Introductionmentioning

confidence: 99%

Balancing Adduct Formation and Ligand Coupling with the Bulky Allyl Complexes [1,3-(SiMe₃)₂C₃H₃]₂M (M = Fe, Co, Ni)

2014

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Passage of CO at atmospheric pressure through solutions of A′ 2 M (M = Fe, Co, Ni; A′ = [1,3-(SiMe 3 ) 2 C 3 H 3 ] − ) in hexanes produces the corresponding allyl complexes A′ 2 Fe(CO) 2 , A′Co(CO) 3 , and A′ 2 Ni(CO), respectively.Although the iron and nickel species can be isolated as pure liquids, the cobalt complex is accompanied by the coupling product 1,3,4,6-tetrakis(trimethylsilyl)-1,5-hexadiene. A′Co(CO) 3 was independently prepared from the reaction of Co 2 (CO) 8 , A′Br, and PhCH 2 N(C 2 H 5 ) 3 + Cl − in aqueous base. The IR stretching frequencies of A′ 2 Fe(CO) 2 and A′Co(CO) 3 are lower than those in the unsubstituted analogues, indicating that the trimethylsilated allyl ligand is a better electron donor than the parent version. Density functional theory calculations were performed on various conformations of the complexes, which reproduced the frequency-lowering effect of the trimethylsilyl groups. They also indicate that the thermodynamics of the formation of A′ 2 Ni(CO) and the unknown (C 3 H 5 ) 2 Ni(CO) are similar, suggesting that the thermal stability of the former is of kinetic origin. Oxidative coupling of the allyl ligands in A′ 2 Fe and A′ 2 Co is induced with I 2 ; this is different from the case with A′ 2 Ni, which has previously been shown to produce the mixed allyl halide complex [A′Ni(μ-I) 2 ] 2 .(2) Article pubs.acs.org/Organometallics

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Section: ■ Introductionmentioning

confidence: 99%

Balancing Adduct Formation and Ligand Coupling with the Bulky Allyl Complexes [1,3-(SiMe₃)₂C₃H₃]₂M (M = Fe, Co, Ni)

2014

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ChemInform Abstract: INSERTION OF ISOCYANIDE AND CARBON MONOXIDE INTO α,Ω‐OCTADIENDIYLNICKEL AND AN ALLENE DERIVED BIS‐Π‐ALLYLNICKEL COMPLEX

Baker¹,

COPELAND²

1977

Chemischer Informationsdienst

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ChemInform Abstract: HYDROFORMYLATION. OXO SYNTHESIS, ROELEN REACTION

Cornils¹

1981

Chemischer Informationsdienst

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Insertion of isocyanide and carbon monoxide into α,ω- octadiendiylnickel and an allene derived bis-π-allylnickel complex

Cited by 14 publications

References 5 publications

Balancing Adduct Formation and Ligand Coupling with the Bulky Allyl Complexes [1,3-(SiMe₃)₂C₃H₃]₂M (M = Fe, Co, Ni)

Balancing Adduct Formation and Ligand Coupling with the Bulky Allyl Complexes [1,3-(SiMe₃)₂C₃H₃]₂M (M = Fe, Co, Ni)

ChemInform Abstract: INSERTION OF ISOCYANIDE AND CARBON MONOXIDE INTO α,Ω‐OCTADIENDIYLNICKEL AND AN ALLENE DERIVED BIS‐Π‐ALLYLNICKEL COMPLEX

ChemInform Abstract: HYDROFORMYLATION. OXO SYNTHESIS, ROELEN REACTION

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Insertion of isocyanide and carbon monoxide into α,ω- octadiendiylnickel and an allene derived bis-π-allylnickel complex

Cited by 14 publications

References 5 publications

Balancing Adduct Formation and Ligand Coupling with the Bulky Allyl Complexes [1,3-(SiMe3)2C3H3]2M (M = Fe, Co, Ni)

Balancing Adduct Formation and Ligand Coupling with the Bulky Allyl Complexes [1,3-(SiMe3)2C3H3]2M (M = Fe, Co, Ni)

ChemInform Abstract: INSERTION OF ISOCYANIDE AND CARBON MONOXIDE INTO α,Ω‐OCTADIENDIYLNICKEL AND AN ALLENE DERIVED BIS‐Π‐ALLYLNICKEL COMPLEX

ChemInform Abstract: HYDROFORMYLATION. OXO SYNTHESIS, ROELEN REACTION

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Balancing Adduct Formation and Ligand Coupling with the Bulky Allyl Complexes [1,3-(SiMe₃)₂C₃H₃]₂M (M = Fe, Co, Ni)

Balancing Adduct Formation and Ligand Coupling with the Bulky Allyl Complexes [1,3-(SiMe₃)₂C₃H₃]₂M (M = Fe, Co, Ni)