Anomalous behaviour of an allyl alcohol in reaction with iron pentacarbonyl

[(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

Author Andrew T. McPhail Chemistry