RING-OPENING REACTIONS OF SOME EPOXIDES WITH CYCLOPENTADIENYLIRON COMPLEXED AMINOARENES

Treatment of a number of CpFe complexed aminoarenes under basic conditions with propylene oxide resulted in ring opening reactions at the primary methylene carbon of the epoxide, leading to the preparation of CpFe complexed N-(2-hydroxypropyl)aminoarenes. Of interest is the formation of a pair of diastereomers in the reaction with the CpFe complex of o-toluidine, demonstrating that besides the chiral center in the N-(2-hydroxylpropyl) group, the CpFe complexed unsymmetrical o-toluidine is also chiral. Similar reactions of the CpFe complexed p-toluidine with cyclohexene oxide or with cis- or trans-2,3-butylene oxide led to ring opening products with the expected stereochemistry from a direct nucleophilic displacement reaction. © 1990.