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Synthesis of 1-Methyl-(1,1) Ferrocenophane

IP.com Disclosure Number: IPCOM000048659D
Original Publication Date: 1982-Mar-01
Included in the Prior Art Database: 2005-Feb-09
Document File: 2 page(s) / 35K

Publishing Venue

IBM

Related People

Mueller-Westerhoff, UT: AUTHOR [+2]

Abstract

We have synthesized a derivative of (1,1) ferrocenophane 1 carrying a SiCl(3) group on one of the bridging methylene groups. This kind of functionalization allows the attachment of ferrocenophane to electrode surfaces. It has become evident, however, that once the molecule is deposited on the surface, the second CH(2) group of the ferrocenophane is quickly oxidized to a ketone, as in 2. Such oxidation may be detrimental to the expected catalytic activity. If a methyl or other alkyl group could be attached at this second methylene bridge, the oxidation would be inhibited. We here describe the synthesis of such a material as an intermediate for the production of stable, functionalized ferrocenophane derivatives.

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Synthesis of 1-Methyl-(1,1) Ferrocenophane

We have synthesized a derivative of (1,1) ferrocenophane 1 carrying a SiCl(3) group on one of the bridging methylene groups. This kind of functionalization allows the attachment of ferrocenophane to electrode surfaces. It has become evident, however, that once the molecule is deposited on the surface, the second CH(2) group of the ferrocenophane is quickly oxidized to a ketone, as in 2. Such oxidation may be detrimental to the expected catalytic activity. If a methyl or other alkyl group could be attached at this second methylene bridge, the oxidation would be inhibited. We here describe the synthesis of such a material as an intermediate for the production of stable, functionalized ferrocenophane derivatives. This material is 1-methyl-(1-1) ferrocenophane, formula 3, which can be obtained from the anion 4 of (1,1) ferrocenophane by reaction with methyl iodide. The deep red anion 4 is prepared in tetrahydrofurane (THF) solution from 1 and butyl lithium. The reaction of 4 with methyl iodide produced 3 as the only product. The new compound is indeed very useful in the synthesis of materials carrying a functional group on one methylene bridge while the other one is blocked by a methyl group. The reaction of 3 with butyl lithium abstracts one proton from the unsubstituted CH(2) group, leading to the anion 5. The reaction of 5 with methyl iodide produces the 1,12-dimethyl (1,1) ferrocenophane 6. Of the two possible isomers of...