Friedel-Crafts alkylation of ferrocene with Z-cyclooctene and cyclohexene

Date

1999-09-15

Author

Grevels, Friedrich-Wilhelm
KURAN, Ayla
Özkar, Saim
Zora, Metin

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

316
views

0
downloads

Cycloalkylated ferrocene derivatives, potentially useful as liquid burning rate modifiers for the HTPB/AP-based composite rocket propellants, were synthesized by the Friedel-Crafts alkylation of ferrocene with Z-cyclooctene or cyclohexene in the presence of AlCl3 as a Lewis acid catalyst. The reaction with Z-cyclooctene yields a mixture of main products containing up to four C8H15 substituents, each of which exists in several isomeric forms, as recognized by MS and GC-MS techniques. Two isomeric monosubstituted products, cyclooctylferrocene and (1-methylcycloheptyl)ferrocene, isolated by means of preparative GC, were identified by C-13-NMR spectroscopy. In the case of cyclohexene, cyclohexylferrocene and a 2:1 mixture of 1,1'-dicyclohexylferrocene and 1,3-dicyclohexylferrocene were isolated and identified by MS and C-13-NMR spectroscopy. (C) 1999 Elsevier Science S.A. All rights reserved.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Materials Chemistry, Biochemistry

URI

https://hdl.handle.net/11511/48297

Journal

Journal of Organometallic Chemistry

DOI

https://doi.org/10.1016/s0022-328x(99)00313-7

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis of ferrocenyl pyrazoles by the reaction of (2-formyl-1-chlorovinyl)ferrocene with hydrazines Zora, Metin (Elsevier BV, 2007-10-15) Synthesis of ferrocenyl-substituted pyrazoles via the reaction between (2-formyl-1-chlorovinyl)ferrocene and hydrazine derivatives is described. Depending upon the substitution pattern of hydrazine, the reaction affords 1-alkyl/aryl-5-ferrocenylpyrazoles and/or 1-alkyl/ aryl-3-ferrocenylpyrazoles. The reaction appears to be general for a variety of hydrazine derivatives.
HINDERED LIGANDS IN TRANSITION-METAL COMPLEXES .39. SYNTHESIS AND DYNAMIC BEHAVIOR OF TETRACARBONYL-ETA-4-TRICYCLO[6.3.0.0(2.7)]UNDECA-3,5-DIENE METAL(0) COMPLEXES AND DICARBONYL-BIS-(ETA-4-TRICYCLO[6.3.0.0(2.7)]UNDECA-3,5-DIENE METAL(0) COMPLEXES OF THE ELEMENTS CHROMIUM, MOLYBDENUM AND TUNGSTEN Özkar, Saim; KREITER, CG (Elsevier BV, 1992-05-01) The hexacarbonyls of chromium, molybdenum, and tungsten react with tricyclo[6.3.0.0(2,7)]undeca-3,5-diene upon UV irradiation in a first step to tetracarbonyl-eta-4-tricyclo[6.3.0.0(2.7)]undeca-3,5-diene-chromium(0) (1), -molybdenum(0) (2) and -tungsten(0) (3). By longer irradiation, dicarbonyl-bis(eta-4-tricyclo[6.3.0.0(2.7)]undeca-3,5-diene)molybdenum(0) (4) and -tungsten(0) (5) are formed. The complexes were purified by chromatography and studied by IR, H-1, and C-13 NMR spectroscopy. The C-13 NMR signal...
Axial water substitution kinetics of sulphato- and hydrogenphosphato-bridged binuclear platinum(III) complexes Camadanli, S; Deveci, N; Gokagac, G; Isci, H (Elsevier BV, 2003-07-22) The kinetics of the axial water substitution reactions for [Pt-2(B-B)(4)(H2O)(2)](2-) (B-B = SO42-, HpO(4)(2-)) with Cl-, Br- and SCN- are reported in acidic aqueous solution. With a large excess of entering ligand and hydrogen ion, only the disubstituted product complex was formed. The reaction rates are first order with respect to the substrate complex and entering ligand and decrease with increasing H+ concentration. In the presence of 0.10 M H+, the rate constants for the replacement of the first water ...
Enantioselective synthesis of both enantiomers of 2-amino-2-(2-furyl)ethan-1-ol as a flexible building block for the preparation of serine and azasugars Demir, Ayhan Sıtkı; Sesenoglu, O; Aksoy-Cam, H; Kaya, H; Aydogan, K (Elsevier BV, 2003-05-16) The selective conversion of 1-(2-furyl)-2-hydroxyethan-1-one and ethyl 2-(2-furyl)-2-oxo acetate into (E)- and (Z)-oximes and oxime ethers followed by oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2-amino-2-(2-furyl)ethan-1-ol with an ee of up to 96%.
A new and efficient chemoenzymatic route to both enantiomers of alpha '-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones Demir, Ayhan Sıtkı; Findik, H; Kose, E (Elsevier BV, 2004-03-08) A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones starting from alpha-methyl-beta-methoxy cyclic enones is reported. Manganese(Ill) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both e...

Citation Formats

F.-W. Grevels, A. KURAN, S. Özkar, and M. Zora, “Friedel-Crafts alkylation of ferrocene with Z-cyclooctene and cyclohexene,” Journal of Organometallic Chemistry, pp. 122–126, 1999, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/48297.