Hydrogenation of Aromatic Ligands During Exchange Reactions Between Ferrocene and Arenes in the Presence of Aluminum Chloride*

Sutherland, R. G.; Pannekoek, Willem‐Jan; Lee, C. C.

doi:10.1111/j.1749-6632.1977.tb41835.x

Cited by 27 publications

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References 15 publications

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“…Other polycyclic aromatic ligands have also been found to give similar hydrogenations (2), and it is of 1 interest to note that in a recent communication on the synthesis of bis(q6-naphthalene)chromium(0) (3),…”

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“…6 : 1 for naphthalene-FcH-A1C13-A1 at 140°C for 4 h in decalin would give a 1 : 1 mixture of the nonhydrogenated and hydrogenated naphthalene and tetralin complexes (2). Using these conditions with 1 instead of naphthalene, only a 6% yield of the q6-4,5,9,10-tetrahydropyrene-trans-bis-q5 -cyclopentadienyliron dication (7) With a molar ratio of 1 : 2 : 2 : 1 for 1-FcH-AlC1,-A1, a reaction carried out in refluxing n-decane (174°C) for 16 h gave a mixture of products from which a 5% yield of the nonhydrogenated dication 5, as its hexafluorophosphate salt, was recovered.…”

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Hydrogenation during ligand exchange reactions between ferrocene and pyrene

Lee¹,

Demchuk²,

Sutherland³

1979

Can. J. Chem.

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. Can. J. Chem. 57,933 (1979).From ligand exchange reactions between ferrocene and pyrene, carried out in the presence of AIC13-AI, the q6-pyrene-q5-cyclopentadienyliron, q6-4,5-dihydropyrene-$-cyclopentadienyliron, and q6-4,5,9,10-tetrahydropyrene-q5-cyclopentadienyliron monocations (2, 3, and 4, respectively) as well as the q6-pyrene-trans-bis-$-cyclopentadienyliron and q6-4,5,9,10-tetrahydropyrene-trans-bis-~-cyclopentadienyIiron dications (5 and 7, respectively) were isolated and identified. A possible mechanism for the partial hydrogenation of the pyrene ligand is discussed.CHOI CHUCK LEE, KEN J. DEMCHUK et RONALD G. SUTHERLAND. Can. J. Chem. 57,933 (1979).A partir de rkactions d'tchange de ligands entre le ferrocene et le pyritne effectutes en presence de AI-AICI, on a pu identifier et caractkriser les monocations q6-pyrtneq5-cyclopentadiknylfer, q6-dihydro-4,5 pyritne q5-cyclopentadiknylfer et q6-tktrahydro-4,5,9,10 pyritne q5-cyclopentadiknylfer (respectivement 2, 3 et 4) ainsi que les dications q6-pyritne trans-bis-q5-cyclopentadiknylfer et q6-tktrahydro-4,5,9,10 pyritne trans-bis-q5-cyclopentadienylfer (respectivement 5 et 7). On discute d'un mkanisme possible pour I'hydrogtnation partielle du ligand pyritne.[ ' it was stated in a footnote that control experiments with naphthalene-AlC1,-A1-CrCl, in C6H5C1 as solvent gave bis(q6-tetralin)chromium(O) as the main product. On the basis of the observation of a stereospecific hydrogenation when 9,lO-dimethylanthracene was the aromatic ligand, a mechanism for the hydrogenation process has also been proposed recently (4). As an extension of these studies, the present work was undertaken on the ligand exchange reaction between ferrocene and pyrene in order to ascertain the extent of hydrogenation that might occur during ligand exchange with this tetracyclic aromatic system. In ligand exchange reactions between ferrocene and phenanthrene, effected in the presence of AIC1,-Al, hydrogenation could take place at the C-9,10 positions giving rise to q6-phenanthrene-q5-cyclo-, pentadienyliron and q6-9,l0-dihydrophenanthrene-1 q5-cy~lopentadien~liron monocations and q6-phenanthrene-trans-bis-q5-cyclopentadienyliron and q6-9,lO-dihydrophenanthrene-trans-bis-q5-cyclopentadienyliron dications (5). In similar reactions with pyrene (I), if analogous partial hydrogenations occur at C-4,5 and C-9,10, monocations 2, 3, and 4, and dications 5, 6, and 7, might be obtained. In the present work, attempts were made to isolate and characterize these cations. The extent of hydrogenation in ligand exchange reactions between ferrocene (FcH) and polycyclic arenes has been found to be highly dependent on reaction conditions such as the molar ratio of the reactants, the reaction temperature and the nature

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Hydrogenation during ligand exchange reactions between ferrocene and pyrene

Lee¹,

Demchuk²,

Sutherland³

1979

Can. J. Chem.

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Iron: Organometallic ChemistryBased in part on the article Iron: Organometallic Chemistry by James R. Green which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

Paley¹

2005

Encyclopedia of Inorganic Chemistry

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Studies involving the preparation, reactivity, and properties of the organometallic complexes of iron (compounds possessing a FeC bond) have played a central role in the growth of organometallics as a major subdiscipline with chemistry. From the discovery of ferrocene in the 1950s to the present day, interest and research activity remain high. This entry provides a survey of this large and diverse area of organometallic chemistry, and is arranged by increasing hapticity of the organic ligand of interest that is bound to iron. Included are discussions of the chemistry of iron σ‐alkyl, acyl, alkynyl, and vinyl complexes, iron carbenes, η1‐ and η3‐allyl iron complexes, η2‐alkene and η4‐diene iron complexes, trimethylenemethane and cyclobutadiene complexes of iron, cationic iron pentadienyl, cyclohexadienyl, and arene complexes, and ferrocenes and heteroferrocenes.

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Iron: Organometallic ChemistryBased in part on the article Iron: Organometallic Chemistry by James R. Green which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

Paley

2005

Encyclopedia of Inorganic and Bioinorganic Chemistry

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Hydrogenation of Aromatic Ligands During Exchange Reactions Between Ferrocene and Arenes in the Presence of Aluminum Chloride*

Cited by 27 publications

References 15 publications

Hydrogenation during ligand exchange reactions between ferrocene and pyrene

Hydrogenation during ligand exchange reactions between ferrocene and pyrene

Iron: Organometallic ChemistryBased in part on the article Iron: Organometallic Chemistry by James R. Green which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

Iron: Organometallic ChemistryBased in part on the article Iron: Organometallic Chemistry by James R. Green which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

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