Structure and Conformational Equilibrium in Substituted [(4-butadiene)Fe(CO)3] Complexes: A Density Functional Study

González-Blanco, Òscar; Branchadell, Vicenç; Grée, René

doi:10.1002/(sici)1521-3765(19990604)5:6<1722::aid-chem1722>3.3.co;2-l

Cited by 7 publications

(8 citation statements)

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“…The structure of 2 is very similar to those previously reported for the (butadiene)Fe(CO) 3 complex 12 and several C 4 -substituted complexes . The bond-shift process between 2 and 2 ‘ involves a rotation of the Fe(CO) 3 group around its pseudo- C 3 axis.…”

Section: Resultssupporting

confidence: 80%

“…(Polyene)iron tricarbonyl complexes are important intermediates in organic synthesis. − The structure and conformational equilibrium of (butadiene)Fe(CO) 3 has been the subject of several theoretical studies. − In particular, the Fe−butadiene bond dissociation energy and the energy barrier for the turnstile rotation computed from density functional calculations are in excellent agreement with the experimental values . More recently, the conformational equilibrium in several carbonyl- and olefin-substituted derivatives of (butadiene)Fe(CO) 3 has also been studied …”

Section: Introductionmentioning

confidence: 78%

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Bond Shift Isomerization in Cyclic and Acyclic (triene)Fe(CO)₃ Complexes. A Density Functional Study

and

Branchadell

2000

Organometallics

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The 1,3-metal shift process has been studied for several conjugated cyclic and acyclic (η 4triene)Fe(CO) 3 systems. In all cases the transition state of the process corresponds to (η 2triene)Fe(CO) 3 structures. The computed energy barriers are notably higher for acyclic complexes than for the cyclic ones, in good agreement with the experimental observations. The analysis of the energy barriers shows that this is due to the different orientations of the triene ligand in the transition states, which leads to more efficient stabilizing metalligand orbital interactions for the cyclic systems.

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Section: Resultssupporting

confidence: 80%

Section: Introductionmentioning

confidence: 78%

Bond Shift Isomerization in Cyclic and Acyclic (triene)Fe(CO)₃ Complexes. A Density Functional Study

and

Branchadell

2000

Organometallics

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“…The substituents at C9 and C12 are not coplanar with the butadiene ligand systems for steric as well as for electronic reasons, as has frequently been observed for butadiene and 1azabutadiene irontricarbonyl complexes, and in accordance with theoretical investigations on several derivatives (Marr & Rockett, 1982;Adams et al, 1988;Imhof et al, 1999;Gonzalez-Blanco & Branchadell 1997;Gonzalez-Blanco et al 1999;Mills & Robinson, 1963). The butadiene system C9 C10-C11 C12 shows a Z,E configuration together with an s-cis configuration with respect to the C10-C11 bond.…”

Section: Commentsupporting

confidence: 83%

Tricarbonyl[η⁴-2-phenyl-4-(3-phenylallylidene)-4H-oxazol-5-one]iron(0)

Imhof

Garms

2005

Acta Cryst E

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The title compound, [Fe(C18H13NO2)(CO)3], is produced by the reaction of Fe2(CO)9 with an azlactone obtained from hippuric acid and cinnamaldehyde. Although, in principle, various coordination sites are possible in the ligand, the 1,3‐butadiene subunit exclusively binds to the transition metal in an η4‐fashion. The crystal structure is stabilized by intermolecular interactions between the O atoms of the lactone and terminal carbon monoxide ligands and various CH groups.

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“…DFT calculations13, 7 predict that the cisoid conformation for the tricarbonyliron complex is about 4 kJ mol −1 more stable than the corresponding transoid one. This is interesting because the transoid conformation is favored for the free [3]dendralene (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Applications of Tricarbonyliron Complexes of Dendralenes

Toombs-Ruane

Osinski

Fallon

et al. 2011

Chemistry An Asian Journal

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[3]Dendralene and [4]dendralene are converted smoothly into tricarbonyliron complexes. The structures of four complexes analyzed by DFT and single-crystal X-ray analysis show that, in contrast to free hydrocarbons, complexed dendralenes prefer a roughly in-plane conformation. The complexes are stable towards Fe(CO)(3) group migration up to 150 °C. The synthetic value of Fe(CO)(3) complexation in the dendralene series is demonstrated through a variety of selective synthetic manipulations (Diels-Alder reaction, dipolar cycloaddition, Simmons-Smith cyclopropanation, dihydroxylation, olefin cross metathesis) that are not achievable by direct transformation of the free hydrocarbons. Application to the synthesis of a previously unreported, highly reactive linear/cross-conjugated hydrocarbon is also described.

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Structure and Conformational Equilibrium in Substituted [(4-butadiene)Fe(CO)3] Complexes: A Density Functional Study

Cited by 7 publications

References 0 publications

Bond Shift Isomerization in Cyclic and Acyclic (triene)Fe(CO)₃ Complexes. A Density Functional Study

Bond Shift Isomerization in Cyclic and Acyclic (triene)Fe(CO)₃ Complexes. A Density Functional Study

Tricarbonyl[η⁴-2-phenyl-4-(3-phenylallylidene)-4H-oxazol-5-one]iron(0)

Synthesis and Applications of Tricarbonyliron Complexes of Dendralenes

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Structure and Conformational Equilibrium in Substituted [(4-butadiene)Fe(CO)3] Complexes: A Density Functional Study

Cited by 7 publications

References 0 publications

Bond Shift Isomerization in Cyclic and Acyclic (triene)Fe(CO)3 Complexes. A Density Functional Study

Bond Shift Isomerization in Cyclic and Acyclic (triene)Fe(CO)3 Complexes. A Density Functional Study

Tricarbonyl[η4-2-phenyl-4-(3-phenylallylidene)-4H-oxazol-5-one]iron(0)

Synthesis and Applications of Tricarbonyliron Complexes of Dendralenes

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Bond Shift Isomerization in Cyclic and Acyclic (triene)Fe(CO)₃ Complexes. A Density Functional Study

Bond Shift Isomerization in Cyclic and Acyclic (triene)Fe(CO)₃ Complexes. A Density Functional Study

Tricarbonyl[η⁴-2-phenyl-4-(3-phenylallylidene)-4H-oxazol-5-one]iron(0)