Synthesis of β-dihydrothebaine

Article abstract of DOI:10.1021/jo00412a043

The authors have found that the reaction of thebaine with K/liquid NH₃ gives a 1:1 mixture of 2 and 3 in 95% yield. It was also observed that treatment of phi-DHT (3) with K/liquid NH₃ in the presence of a catalytic amount of Fe(NO₃)₃ x 9H₂O⁷ gave a 1:1 mixture of 2 and 3 in 79% yield. These results suggest that an intermediate dianion 5 is formed which is protonated either at C₅ or C₇.