Browse Prior Art Database

1-Methyl- 12-Vinylidene- (1.1) Ferrocenophane

IP.com Disclosure Number: IPCOM000050364D
Original Publication Date: 1982-Oct-01
Included in the Prior Art Database: 2005-Feb-10
Document File: 2 page(s) / 36K

Publishing Venue

IBM

Related People

Mueller-Westerhoff, UT: AUTHOR [+2]

Abstract

Derivatives of (1.1)ferrocenophane, which carry a reactive olefin function at one of the bridges, are useful in attaching the ferrocenophane system to various semiconductor surfaces. However, once the material is deposited on the surface, the second bridge can rapidly become oxidized unless it is protected by a methyl group. The compound 1-methyl 12-vinyliden-(1.1) ferrocenophane 1 is such a material, possessing increased resistance to oxidation.

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1-Methyl- 12-Vinylidene- (1.1) Ferrocenophane

Derivatives of (1.1)ferrocenophane, which carry a reactive olefin function at one of the bridges, are useful in attaching the ferrocenophane system to various semiconductor surfaces. However, once the material is deposited on the surface, the second bridge can rapidly become oxidized unless it is protected by a methyl group. The compound 1-methyl 12-vinyliden-(1.1) ferrocenophane 1 is such a material, possessing increased resistance to oxidation.

There are two independent methods of the synthesis of the olefin 1. In the first one, the compound 1 can be obtained in two steps, starting from 1-methyl- (1.1) ferrocenophane 2. In chloroform solution, 2 is oxidized by MnO(2) at the unsubstituted bridge to form the ketone 3. The cleanness of this reaction shows that a methyl group indeed protects the bridge positions of (1.1) ferrocenophane. The ketone can be converted to the olefin 1 by a Wittig reaction with (C(6)H(5))(3)PCH(2). The reaction is complete after one hour reflux in methylene chloride. The product 1 forms red crystals. In solution, 1 tends to polymerize rapidly.

A much more efficient and convenient way of preparing 1 starts from 1,12- dimethyl-(1.1)ferrocenophane 4. The synthesis of this material has recently been described (Cassens, Eilbracht, Nazzal, Proessdorf and Mueller-Westerhoff, J. Am. Chem. Soc. 103, 6367 (1981)). From either the exo- or the endo-isomer of 4 or from any mixture thereof, the carbocation...