Regioselective synthesis of several heterocyclic fused azepines using diisobutylaluminum hydride

Article abstract of DOI:10.3987/COM-98-8104

5,6,7,8-Tetrahydrothieno[3,2-b]azepine,5,6,7,8-tetrahydro-1H-furo[3,2-b] azepine, and 1,4,5,6,7,8-hexahydropyrrolo[3,2-b]azepine were synthesized by the ring expansion reaction of heterocyclic fused cyclohexanone oximes with diisobutylaluminum hydride (DIBAH). The mechanism of the reaction was different from that of Beckmann rearrangement.