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Synthesis 1992; 1992(11): 1096-1098
DOI: 10.1055/s-1992-26313
short paper
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Ein einfacher Weg zu 1,2,3,4-Tetramethylfulven und zu 1-funktionalisierten 2,3,4,5-Tetramethylcyclopentadienen

P. Jutzi* , T. Heidemann, B. Neumann, H. G. Stammler
  • *Fakultät für Chemie der Universität Bielefeld, Universitätsstraße, D-4800 Bielefeld 1, Germany
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Publication Date:
17 September 2002 (online)

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A Simple Route to 1,2,3,4-Tetramethylfulvene and to 1-Functionalized 2,3,4,5-Tetramethylcyclopentadienes 5-Bromo-1,2,3,4,5-pentamethylcyclopenta-1,3-diene, which is available in good yield from 1,2,3,4,5-pentamethylcyclopenta-1,3-diene, reacts with potassium tert-butoxide in the presence of catalytic amounts of 18-crown-6 under dehydrobromination to give 1,2,3,4-tetramethylfulvene (1,2,3,4-methyl-5-methylenecyclopenta-1, 3-di-ene, 1) in high yield. Compound 1 can be used to prepare various 1-functionalized 2,3,4,5-tetramethylcyclopentadiene systems. For example, reaction of lithium dimethylamide, allylmagnesium chloride, potassium indenide or 1,3-dithian-2-yllithium with 1 leads, after hydrolysis, to the corresponding substituted cyclopentadiene systems 3-6 in high yield.