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

Date

1999-09-15

Author

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

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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

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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.