A rapid approach to ferrocenophanes via ring-closing metathesis

Locke, Andrew J.; Jones, Carl J.; Richards, Christopher J.

doi:10.1016/s0022-328x(01)00980-9

Cited by 54 publications

(27 citation statements)

References 23 publications

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“…In 2001, Richards and co‐workers reported a novel synthetic method of [4]ferrocenophanes A (M=Fe) by the ring‐closing metathesis (RCM) reaction of 1,1′‐diallylferrocenes using the Grubbs catalyst 8. Shortly after this report, we independently found analogous reactions and reported that the metathesis route could be applied to the preparation of various bridged metallocenes of group 8 metals A (ferrocenes, ruthenocenes)9 and of group 4 metals B (zirconocene dichlorides, hafnocene dichlorides) 9a.…”

Section: Introductionmentioning

confidence: 99%

A Continuous Flow Strategy for the Coupled Transfer Hydrogenation and Etherification of 5‐(Hydroxymethyl)furfural using Lewis Acid Zeolites

et al. 2014

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Hf-, Zr- and Sn-Beta zeolites effectively catalyze the coupled transfer hydrogenation and etherification of 5-(hydroxymethyl)furfural with primary and secondary alcohols into 2,5-bis(alkoxymethyl)furans, thus making it possible to generate renewable fuel additives without the use of external hydrogen sources or precious metals. Continuous flow experiments reveal nonuniform changes in the relative deactivation rates of the transfer hydrogenation and etherification reactions, which impact the observed product distribution over time. We found that the catalysts undergo a drastic deactivation for the etherification step while maintaining catalytic activity for the transfer hydrogenation step. (119) Sn and (29) Si magic angle spinning (MAS) NMR studies show that this deactivation can be attributed to changes in the local environment of the metal sites. Additional insights were gained by studying effects of various alcohols and water concentration on the catalytic reactivity.

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Section: Introductionmentioning

confidence: 99%

A Continuous Flow Strategy for the Coupled Transfer Hydrogenation and Etherification of 5‐(Hydroxymethyl)furfural using Lewis Acid Zeolites

et al. 2014

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“…Optically active ( S , S )‐ 3 was synthesized from ( R , R )‐1,1′‐bis(1‐acetoxyethyl)ferrocene ( R , R )‐ 5 in four steps (Scheme ). The stereospecific vinylation11 of (( R , R )‐ 5 ) and subsequent kinetic resolution in the ring‐closing metathesis gave ( S , S )‐ 6 and meso ‐ 7 12. Hydroboration of the mixtures with 9‐borabicyclo[3.3.1]nonane (9‐BBN), followed by treatment by aqueous NaOH and H 2 O 2 , afforded the corresponding diol ( S , S )‐ 8 , whilst meso ‐ 7 did not react under these conditions.…”

Section: Methodsmentioning

confidence: 99%

A Chiral Concave‐Bound Cyclopentadienyl Iron Complex of Sumanene

et al. 2009

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Schale mit zwei Seiten: In zwei [CpFe(η6‐Sumanen)]+‐Komplexen, in denen sich die CpFe‐Einheit an der konkaven Seite des schalenförmigen π‐Systems befindet, ist die Rotation des monoalkylierten Cyclopentadienyl(Cp)‐Rings gehindert. Für den MeCpFe‐Komplex wurde im Festkörper eine asymmetrische Stapelung von Atropisomeren beobachtet, und im (S)‐sBuCpFe‐Komplex – dem ersten chiralen Komplex mit einer π‐Schale als Ligand – war der Sumanenligand magnetisch und optisch desymmetrisiert (siehe Bild).

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“…Chemie was synthesized from (R,R)-1,1'-bis(1-acetoxyethyl)ferrocene (R,R)-5 in four steps (Scheme 1 b). The stereospecific vinylation [11] of ((R,R)-5) and subsequent kinetic resolution in the ring-closing metathesis gave (S,S)-6 and meso-7. [12] Hydroboration of the mixtures with 9-borabicyclo[3.3.1]nonane (9-BBN), followed by treatment by aqueous NaOH and H 2 O 2 , afforded the corresponding diol (S,S)-8, whilst meso-7 did not react under these conditions.…”

Section: Methodsmentioning

confidence: 99%

A Chiral Concave‐Bound Cyclopentadienyl Iron Complex of Sumanene

et al. 2009

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Great bowls of fire: The rotation of the cyclopentadienyl (Cp) ring is restricted in two concave-bound monoalkyl-substituted [CpFe(eta(6)-sumanene)](+) "pi-bowl" complexes (see picture). The asymmetric stacking of atropisomers was observed with a MeCpFe complex in the solid state and the chiral (S)-sBuCpFe complex showed magnetic and optical desymmetrization of the sumanene ligand, which is the first example of a chiral complex of a pi-bowl ligand.

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A rapid approach to ferrocenophanes via ring-closing metathesis

Cited by 54 publications

References 23 publications

A Continuous Flow Strategy for the Coupled Transfer Hydrogenation and Etherification of 5‐(Hydroxymethyl)furfural using Lewis Acid Zeolites

A Continuous Flow Strategy for the Coupled Transfer Hydrogenation and Etherification of 5‐(Hydroxymethyl)furfural using Lewis Acid Zeolites

A Chiral Concave‐Bound Cyclopentadienyl Iron Complex of Sumanene

A Chiral Concave‐Bound Cyclopentadienyl Iron Complex of Sumanene

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