Bis(pentamethylcyclopentadienyl)methanol: Synthese, Struktur und Derivatisierung

Jutzi P, Mix A, Lindermeier T, Stammler H-G, Neumann B (1994)
Chemische Berichte 127(1): 107-112.

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Journal Article | Published | German
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BIS(PENTAMETHYLCYCLOPENTADIENYL)METHANOL - SYNTHESIS, STRUCTURE, AND DERIVATIZATION
Abstract
Bis(pentamethylcyclopentadienyl) ketone (1) reacts at low temperatures with LiAlH4 to form in good yields (pentamethylcyclopentadienyl)methanol (2) and its corresponding intramolecular Diels-Alder product 3 in a ca. 2:1 ratio. The alcohol 2 is separated from the tetracyclic compound 3 by crystallisation at -70°C from hexane/pyridine as pyridine adduct. The pyridine-free alcohol 2 is available by repeated dissolving of the adduct in hexane and removal of the volatile components in vacuo. The alcohol tends to intramolecular [4 + 2] cycloaddition even at room temperature with formation of 3. A derivatization of 2 is possible by deprotonation with alkyllithium compounds, which leads to the alcoholate 4, and subsequent treatment with phosgen and tosyl chloride, thus affording the chloroformate 6 and the tosylate 7, respectively, in good yields. The thermolabile tosylate 7 decomposes to pentamethylbenzene or, under basic conditions, to the pentacyclic compound 7.
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Jutzi P, Mix A, Lindermeier T, Stammler H-G, Neumann B. Bis(pentamethylcyclopentadienyl)methanol: Synthese, Struktur und Derivatisierung. Chemische Berichte. 1994;127(1):107-112.
Jutzi, P., Mix, A., Lindermeier, T., Stammler, H. - G., & Neumann, B. (1994). Bis(pentamethylcyclopentadienyl)methanol: Synthese, Struktur und Derivatisierung. Chemische Berichte, 127(1), 107-112.
Jutzi, P., Mix, A., Lindermeier, T., Stammler, H. - G., and Neumann, B. (1994). Bis(pentamethylcyclopentadienyl)methanol: Synthese, Struktur und Derivatisierung. Chemische Berichte 127, 107-112.
Jutzi, P., et al., 1994. Bis(pentamethylcyclopentadienyl)methanol: Synthese, Struktur und Derivatisierung. Chemische Berichte, 127(1), p 107-112.
P. Jutzi, et al., “Bis(pentamethylcyclopentadienyl)methanol: Synthese, Struktur und Derivatisierung”, Chemische Berichte, vol. 127, 1994, pp. 107-112.
Jutzi, P., Mix, A., Lindermeier, T., Stammler, H.-G., Neumann, B.: Bis(pentamethylcyclopentadienyl)methanol: Synthese, Struktur und Derivatisierung. Chemische Berichte. 127, 107-112 (1994).
Jutzi, Peter, Mix, Andreas, Lindermeier, Tanja, Stammler, Hans-Georg, and Neumann, Beate. “Bis(pentamethylcyclopentadienyl)methanol: Synthese, Struktur und Derivatisierung”. Chemische Berichte 127.1 (1994): 107-112.
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