Download PDF
Synthesis 1992; 1992(11): 1096-1098
DOI: 10.1055/s-1992-26313
short paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.

      >