Anomalous behaviour of an allyl alcohol in reaction with iron pentacarbonyl |
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| Authors: | J.C. Barborak S.L. Watson A.T. McPhail R.W. Miller |
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| Affiliation: | Department of Chemistry, University of North Carolina at Greensboro, Greensboro, North Carolina 27412 U.S.A.;Department of Chemistry, Duke University, Durham, North Carolina 27706 U.S.A. |
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| 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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