Abstract
Examinations were made on the Grignard reaction of N-methyl-4-anisoyl-10-hydroxy-decahydroisoquinoline (IVα) and its isomer (IVβ). (IVα) formed the Grignard reaction product (XIIα), while (IVβ) afforded (XIIβ) and its diasteromer (XIIβ′). Dehydration of (XIIα), (XIIβ), and (XIIβ′) in acetic acid with sulfuric acid resulted in the formation of identical substance (XIII) from any of them. From its analytical values, ultraviolet absorption spectrum, and the result of ozonolysis, (XIII) was found to have a styrene-type structure. Acetylation of the alpha-type (XIIα) was found to result in acetylation of only the angular hydroxyl to form (XVα), which easily underwent dehydration on being heated in acid medium and produced (XVI) with a styrene-type structure. Acetylation was not effected in the beta-type (XIIβ) and the starting material was recovered. A more drastic conditions of acetylation showed formation of (XIII). Such a difference in the reactivity of alpha- and beta-type compounds is probably due to the difference in their steric configurations. It was proved that it is impossible to effect mutual isomerization among the Grignard reaction products (XIIα), (XIIβ), and (XIIβ′), which endorses the appropriateness of the assumption made earlier regarding the mechanism of isomerization.
