| Abstract: | The condensation of naphthalene-1- or 2-carbaldehyde with dimethyl 2,2-dimethyl-succinate (Stobbe conditions) gives predominantly the ( Z )-hemiesters 3 and 11a . The hemiester 3 contains a small amount of the ( E )-isomer. Similar condensation of naphthalene-2-carbaldehyde with dimethyl-2-methylsuccinate gave the hemiester ( E )- 12a . Their configuration and the ratios of the ( Z:E )-hemiesters, their derived acids, anhydrides, indenones and phenanthrene derivatives are inferred by high resolution 1H-n.m.r. spectroscopy. |
