SYNTHESIS AND REACTIVITY OF -2,3,5,6-TETRAHYDRO-1H-1,4-ETHANOBENZO[F]QUINOLINE - X-RAY MOLECULAR-STRUCTURE OF 6,10B-HEXAHYDRO-1H-1,4-ETHANOBENZO[F]QUINOLIN-6-YL ACETATE

Cyclocondensation of 2-(2-cyano-1,2-diphenylethyl)quinuclidin-3-one 1 in the presence of sulfuric acid gave an intramolecular phenylation in stead of lactam formation. The cyclic product was hydrogenated to give henyl-2,3,4a,5,6,10b-hexahydro-1H-1,4-ethanobenzo- [f]quinoline. On t reatment with LiAIH(4) the carbamoyl group was stereospecifically repl aced by a hydroxy group. The alcohol was acetylated and the structure was confirmed by X-ray crystallography. The hydroxylation reaction is believed to proceed via a carbonitrile intermediate. In the presence o f air the nitrile can be converted to a ketone which is then reduced t o the alcohol with an overall retention of configuration.