Cycloadditions of Isocyanides to Azomethine Ylides. Synthesis and Properties of 1-Phthalimidoazetidines

Article abstract of DOI:10.1021/jo00152a014

Reactions of isocyanides with 1-phthalimidoaziridines 1,5, and 11 gave 1-phthalimidoazetidines by <1+3> cycloaddition to the azomethine ylides that are in equilibrium with the aziridines. (tert-Butylimino)azetidines and (tert-octylimino)azetidines rearranged into open-chain azadienes.Reactions of hydrazine hydrate with 1-phthalimidoazetidines did not give the corresponding N-aminoazetidines, but rather their decomposition products, nitrogen and enamino esters.