Bridged ferrocenes. VI. Hydrogenation with Pd/C catalyst

Manny Hillman, Barry Gordon, Nan Dudek, Ruby Fajer, Etsuko Fujita, Jeffrey Gaffney, Phelesia Jones, Allen J. Weiss, Shozo Takagi

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14 Citations (Scopus)

Abstract

The method of Van Meurs et al. [1] for hydrogenation of ferrocene has been extended to include a variety of bridged ferrocenes. Singly bridged and dibridged ferrocenes containing tri-, tetra-, or pentamethylene bridges were hydrogenated to the corresponding polycyclic hydrocarbons. Conditions required were consistent with a mechanism that involves an initial protonation of the iron atom. Bridge opening to a propylferrocene derivative was observed for the compound with three not-all adjacent trimethylene bridges, and no hydrogenation reaction was observed for the corresponding derivative with tetramethylene bridges. Without catalyst or hydrogen, trifluoroacetylation and a rearrangement of a bridge were observed in the tris(trimethylene) compound. In the presence of catalyst but no hydrogen, an alpha alcohol and the corresponding diferrocenyl ether were obtained. Possible mechanisms are suggested for these reactions.

Original languageEnglish
Pages (from-to)229-256
Number of pages28
JournalJournal of Organometallic Chemistry
Volume194
Issue number2
DOIs
Publication statusPublished - 1980

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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    Hillman, M., Gordon, B., Dudek, N., Fajer, R., Fujita, E., Gaffney, J., Jones, P., Weiss, A. J., & Takagi, S. (1980). Bridged ferrocenes. VI. Hydrogenation with Pd/C catalyst. Journal of Organometallic Chemistry, 194(2), 229-256. https://doi.org/10.1016/S0022-328X(00)86672-3