Development of a convenient new synthetic route to [3]ferrocenophanones |
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Authors: | Tebben Ludger Neumann Markus Kehr Gerald Fröhlich Roland Erker Gerhard Losi Serena Zanello Piero |
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Affiliation: | Organisch-Chemisches Institut der Universit?t Münster, Corrensstr. 40, D-48149, Münster, Germany. |
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Abstract: | [3]Ferrocenophanone rac-8 was prepared by several non-Friedel-Crafts pathways starting from a Mannich-type coupling of 1,1'-diacetylferrocene followed by catalytic hydrogenation. Hydride abstraction from the resulting alpha-dimethylamino[3]ferrocenophane rac-14 with B(C6F5)3 followed by hydrolysis gave the ketone rac-8. Several variants of the Sommelet reaction, using ethylglyoxylate, formaldehyde or hexamethylenetetramine (urotropine) as the "oxidizing" reagent gave the alpha-[3]ferrocenophanone 8 in good to excellent yield. Some variants of these reactions were also used for the preparation of the pure enantiomer (R)-8. The electrochemical behaviour of 8 has been investigated and compared with related derivatives. |
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