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Anomalous behaviour of an allyl alcohol in reaction with iron pentacarbonyl

Authors
Journal
Journal of Organometallic Chemistry
0022-328X
Publisher
Elsevier
Publication Date
Volume
185
Issue
3
Identifiers
DOI: 10.1016/s0022-328x(00)83517-2
Disciplines
  • Chemistry

Abstract

Abstract [(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.

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