GAMMA,GAMMA-DISUBSTITUTED ITACONIC ACIDS .1. STOBBE CONDENSATION OF 1-ARYLNAPHTHYL KETONES WITH DIETHYL SUCCINATE

Arylnaphthyl ketones condense with diethyl succinate yielding the stereoisomeric half‐esters 2a–2d which were subjected to a series of reactions leading to 1‐phenylphenanthrene and 1,1′‐binaphthyl derivatives. (E)‐3‐Ethoxycarbonyl‐4‐(4‐methoxynaphth‐1‐yl)‐4‐arylbut‐3‐enoic acids (2b–d) were converted finally into the corresponding naphtho[1,2‐c]fluorenones (9). The structure of the products was established by IR. and UV. spectroscopy. The effect of substituents on the relative proportions of (E)‐ and (Z)‐half‐esters 2 was determined by chromatography and UV. spectroscopy. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim