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

Research output: Contribution to journalArticle

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 - Jan 1 1980

Fingerprint

Hydrogenation
Catalysts
Hydrogen
Cyclic Hydrocarbons
Derivatives
Protonation
Ether
Ethers
Alcohols
Iron
Hydrocarbons
Atoms
cyclopropane

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Hillman, M., Gordon, B., Dudek, N., Fajer, R., Fujita, E., Gaffney, 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

Bridged ferrocenes. VI. Hydrogenation with Pd/C catalyst. / Hillman, Manny; Gordon, Barry; Dudek, Nan; Fajer, Ruby; Fujita, Etsuko; Gaffney, Jeffrey; Jones, Phelesia; Weiss, Allen J.; Takagi, Shozo.

In: Journal of Organometallic Chemistry, Vol. 194, No. 2, 01.01.1980, p. 229-256.

Research output: Contribution to journalArticle

Hillman, M, Gordon, B, Dudek, N, Fajer, R, Fujita, E, Gaffney, J, Jones, P, Weiss, AJ & Takagi, S 1980, 'Bridged ferrocenes. VI. Hydrogenation with Pd/C catalyst', Journal of Organometallic Chemistry, vol. 194, no. 2, pp. 229-256. https://doi.org/10.1016/S0022-328X(00)86672-3
Hillman, Manny ; Gordon, Barry ; Dudek, Nan ; Fajer, Ruby ; Fujita, Etsuko ; Gaffney, Jeffrey ; Jones, Phelesia ; Weiss, Allen J. ; Takagi, Shozo. / Bridged ferrocenes. VI. Hydrogenation with Pd/C catalyst. In: Journal of Organometallic Chemistry. 1980 ; Vol. 194, No. 2. pp. 229-256.
@article{aff7a099a6e040eb8f75e84263755825,
title = "Bridged ferrocenes. VI. Hydrogenation with Pd/C catalyst",
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.",
author = "Manny Hillman and Barry Gordon and Nan Dudek and Ruby Fajer and Etsuko Fujita and Jeffrey Gaffney and Phelesia Jones and Weiss, {Allen J.} and Shozo Takagi",
year = "1980",
month = "1",
day = "1",
doi = "10.1016/S0022-328X(00)86672-3",
language = "English",
volume = "194",
pages = "229--256",
journal = "Journal of Organometallic Chemistry",
number = "2",

}

TY - JOUR

T1 - Bridged ferrocenes. VI. Hydrogenation with Pd/C catalyst

AU - Hillman, Manny

AU - Gordon, Barry

AU - Dudek, Nan

AU - Fajer, Ruby

AU - Fujita, Etsuko

AU - Gaffney, Jeffrey

AU - Jones, Phelesia

AU - Weiss, Allen J.

AU - Takagi, Shozo

PY - 1980/1/1

Y1 - 1980/1/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85025782924&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85025782924&partnerID=8YFLogxK

U2 - 10.1016/S0022-328X(00)86672-3

DO - 10.1016/S0022-328X(00)86672-3

M3 - Article

AN - SCOPUS:85025782924

VL - 194

SP - 229

EP - 256

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 2

ER -