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Anomalous behaviour of an allyl alcohol in reaction with iron pentacarbonyl

Publication ,  Journal Article
Barborak, JC; Watson, SL; McPhail, AT; Miller, RW
Published in: Journal of Organometallic Chemistry
February 12, 1980

[(6,7,8,9-η)-Bicyclo[3.2.2]nona-2,6,8-trien-4-ol]tricabonyliron (6) rearranges in the presence of Fe(CO)5 to [(2,3,6,7-η)-bicyclo[3.2.2]nona-2,6,8-trien-4-one] tricarbonyliron (7); rather than [(6,7,8,9-η)-bicyclo-[3.2.2]nona-6,8-dien-2-one] tricarbonyliron (9), the product expected on the basis of known organoiron chemistry and previously proposed mechanisms. The starting material 6 is stable in the absence of Fe(CO)5, which leads to the conclusion that some iron-containing species derived from fe(CO)5 is responsible for bringing about rearrangement. Since the usual mechanism for iron carbonyl-induced rearrangement in olefins cannot be operating here, a mechanism involving an ion pair with [HFe(CO)4]- is suggested. © 1980.

Duke Scholars

Published In

Journal of Organometallic Chemistry

DOI

ISSN

0022-328X

Publication Date

February 12, 1980

Volume

185

Issue

3

Related Subject Headings

  • Organic Chemistry
  • 3403 Macromolecular and materials chemistry
  • 3402 Inorganic chemistry
  • 0399 Other Chemical Sciences
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry
 

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Barborak, J. C., Watson, S. L., McPhail, A. T., & Miller, R. W. (1980). Anomalous behaviour of an allyl alcohol in reaction with iron pentacarbonyl. Journal of Organometallic Chemistry, 185(3). https://doi.org/10.1016/S0022-328X(00)83517-2
Barborak, J. C., S. L. Watson, A. T. McPhail, and R. W. Miller. “Anomalous behaviour of an allyl alcohol in reaction with iron pentacarbonyl.” Journal of Organometallic Chemistry 185, no. 3 (February 12, 1980). https://doi.org/10.1016/S0022-328X(00)83517-2.
Barborak JC, Watson SL, McPhail AT, Miller RW. Anomalous behaviour of an allyl alcohol in reaction with iron pentacarbonyl. Journal of Organometallic Chemistry. 1980 Feb 12;185(3).
Barborak, J. C., et al. “Anomalous behaviour of an allyl alcohol in reaction with iron pentacarbonyl.” Journal of Organometallic Chemistry, vol. 185, no. 3, Feb. 1980. Scopus, doi:10.1016/S0022-328X(00)83517-2.
Barborak JC, Watson SL, McPhail AT, Miller RW. Anomalous behaviour of an allyl alcohol in reaction with iron pentacarbonyl. Journal of Organometallic Chemistry. 1980 Feb 12;185(3).
Journal cover image

Published In

Journal of Organometallic Chemistry

DOI

ISSN

0022-328X

Publication Date

February 12, 1980

Volume

185

Issue

3

Related Subject Headings

  • Organic Chemistry
  • 3403 Macromolecular and materials chemistry
  • 3402 Inorganic chemistry
  • 0399 Other Chemical Sciences
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry