γγ‐Disubstituted Itaconic Acids. Part 1. The <i>Stobbe</i> condensation of 1‐arylnaphthyl ketones with diethyl succinate

Abstract

Abstract 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.