Novel analgesics and molecular rearrangements in the morphine–thebaine group. Part XX. Reaction of 7β-cyano-6,14-endo-etheno-7α-methyl-6,7,8,14-tetrahydrothebaine with phenylmagnesium bromide
Abstract
7β-Cyano-6,14-endo-etheno-7α-methyl-6,7,8,14-tetrahydrothebaine (1) on treatment with phenylmagnesium bromide gives the expected imine (2) and a C-4 phenolic by-product (4). Fission of the bicyclo-octene system accompanies acid hydrolysis of the imine.