Journal of Organometallic Chemistry p. 343 - 370 (1989)
Update date:2022-08-03
Topics:
Rodriguez, J.
Brun, P.
Waegell, B.
A series of various, functionnalized 4-vinylcyclohexene derivatives, substituted with electron-withdrawing or -donating groups on the exocyclic double bond, have been isomerized by pentacarbonyliron, under thermodynamic control with heating, into a mixture of conjugated cyclohexadiene tricarbonyliron complexes, of which the 2-substituted derivative is the predominant.When ferrous chloride is used as the co-catalyst, the isomerisation proceeds under kinetic control to give the 1-substituted cyclohexadienetricarbonyliron complex as the major derivative.Reaction mechanisms, have been proposed for these isomerisation processes, which provide a new selective route to such derivatives.The formation of η4-1,4-cyclohexadienetricarbonyl complexes as intermediates has been excluded, and it is shown that the thermal isomerisation proceeds via η2-complexes that are formed by successive 1,3-hydrogen shifts.
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