Y. Becker, A. Eisenstadt, Y. Shvo
1974
Citations
0
Influential Citations
21
Citations
Journal
Tetrahedron
Abstract
Abstract The reactivity of the bond towards diironnonacarbonyl was investigated. 3,6-Dihydro and tetrahydro-1,2-oxazines were used as model compounds. Reduction of the bond predominates in presence of water, while under anydrous conditions a CO insertion into the bond of tetrahydro-1,2-oxazine takes place. The 3,6-dihydro-1,2-oxazine in the presence of Fe2(CO)9 and water, yield π-allyl-Fe-σ-lactones. Carbon dioxide and aniline are also formed in this reaction. The amino alcohol 7 is an intermediate in this and analogous reactions. The lactone 3 under Al2O3 catalysis reacts with primary amines to yield the corresponding lactams. Mechanistic investigation of this reaction points towards a SN2′-like mechanism inasmuch as the attack of the base occurs on the terminal carbon of the π-allyl system. The lactam 4 could be readily converted into the complex π-crotonylideneaniline iron tricarbonyl for which an intramolecular 1,4-H shift was demonstrated by a labeling experiment with deuterium.