Abstract
The reaction of dicymantrenyl ketone with the Grignard reagent 2,4,6-Me3C6H2MgBr in THF occurs as the insertion of the mesityl substituent in the α-position of one of the cyclopentadienyl rings to give (2-mesitylcymantrenyl) cymantrenyl ketone (4), rather than as addition at the C=O group. Reduction of4 by NaBH4 in a THF-EtOH mixture affords (2-mesitylcymantrenyl)cymantrenylmethanol (5). Ionic hydrogenation of5 with the HSiEt3/CF3COOH system gives (2-mesitylcymantrenyl)cymantrenylmethane (7). The structure of alcohol5 has been established by X-ray diffraction analysis.
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References
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 723–728, April, 1994.
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Loim, N.M., Ginzburg, A.G., Batsanov, A.S. et al. Reaction of dicymantrenylketone with mesitylmagnesium bromide. Russ Chem Bull 43, 675–680 (1994). https://doi.org/10.1007/BF00699847
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DOI: https://doi.org/10.1007/BF00699847