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The full details of investigations into the regiochemistry and stereochemistry of iron-catalyzed carbocyclizations of 2,7,9-decatriene derivatives to form five-membered carbocyclic ring systems are described. The roles of the allylic substituent, the alkene geometry, diene substitution, and the influence of resident stereogenic centers incorporated in the tether chain connecting the reacting 1,3-diene and alkene subunits are discussed.

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The methyl (la) and the phenyl (2) derivatives of (Z)-4-benzylideneoxazolin-5-one were hydrolyzed at comparable rates under alkaline conditions. In contrast, the acidic hydrolysis of 2 was at least 105 times slower than that of la. The Hammett p value obtained from the acidic hydrolysis of the phenyl substituted derivatives of la was 0.20 ± 0.09 while that from the corresponding basic hydrolysis was 1.50 ± 0.11. Methanolysis of la under basic conditions produced the methyl ester of (Z)-a-(acetylamino)cinnamic acid, and that under acidic conditions led to products consistent with the attack of methanol at the imine carbon. These results indicate that the alkaline hydrolysis of the oxazolin-5-one derivatives occurs through nucleophilic attack at the carbonyl carbon of the substrate and the acidic hydrolysis through that at the imine carbon.