Novel analgesics and molecular rearrangements in the morphine–thebaine group. Part XXVI. Some reactions of the thebaine–2-chloroacrylonitrile adduct

Abstract

Catalytic hydrogenation and treatment with nucleophiles (Grignard reagent, alkoxide ions, morpholine) results in loss of chlorine from the thebaine–2-chloroacrylonitrile adduct. The products of the latter reactions are derived from the C-7 carbanion (5) and the 7,8-unsaturated 7-carbonitrile (9), in most cases by processes involving rearrangements.