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Mono- and Diolefins Derived From (1.1) Ferrocenophanes

IP.com Disclosure Number: IPCOM000050363D
Original Publication Date: 1982-Oct-01
Included in the Prior Art Database: 2005-Feb-10
Document File: 2 page(s) / 51K

Publishing Venue

IBM

Related People

Mueller-Westerhoff, UT: AUTHOR [+2]

Abstract

Derivatives of (1.1)ferrocenophane, in which one or both of the bridges have been converted into olefin groups, are useful in the formation of polymers or copolymers and of other reactive derivatives. They also can be used for plasma polymerization reactions. These materials have now been obtained in high yield through a Wittig reaction of the corresponding ketones. The latter were prepared by oxidation of the parent (1.1)ferrocenophane.

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Mono- and Diolefins Derived From (1.1) Ferrocenophanes

Derivatives of (1.1)ferrocenophane, in which one or both of the bridges have been converted into olefin groups, are useful in the formation of polymers or copolymers and of other reactive derivatives. They also can be used for plasma polymerization reactions. These materials have now been obtained in high yield through a Wittig reaction of the corresponding ketones. The latter were prepared by oxidation of the parent (1.1)ferrocenophane.

Since there has now been developed an efficient method for the synthesis of the parent (1.1)ferrocenophane, one can now obtain these ketones by oxidation with MnO(2) in chloroform. This procedure affords both ketones, which can be separated by column chromatography.

To specifically prepare the mono-ketone 1, convert the ferrocenophane into the carbocation, hydrolyze this to the carbinol, and oxidize the carbinol to the mono-ketone under such mild conditions that only small amounts of the diketone are produced as a byproduct.

The conversion of the ketones 1 and 2 to the mono-olefin 3 and the diolefin 4, respectively, is accomplished through a Wittig reaction using (C(6)H(5))(3)PCH(2). The reaction of 1 with the ylid proceeds smoothly in THF during two hours. Because 2 is a very insoluble and unreactive material, its reaction with the ylid requires the more drastic conditions of 24 hours reflux in THF. Both reactions yield the corresponding olefins in high yield.

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