Studies on keten and its derivatives. Part 86. Photoreaction of diketen with dimedone and isophorone

Abstract

Photoreaction of diketen with dimedone (1) gave 1-hydroxy-4,4-dimethyl-2,6-dioxocyclo-octan-1-ylacetic acid β-lactone (2) and 4,4-dimethyl-2,6-dioxobicyclo[5.1.0]octan-1-ylacetic acid (3). A similar reaction of isophorone (6) gave 8-hydroxy-4,4,6-trimethyl-2-oxo-cis-bicyclo[4.2.0]octan-8-ylacetic acid β-lactone (7a, b), and an oil, which, on treatment with aniline, gave 7-hydroxy-4,4,6-trimethyl-2-oxo-cis-bicyclo[4.2.0]octan-7-ylacetanilide (11a, b). Reaction of compounds (7a) and (7b) with aniline gave 3-anilino-1-hydroxy-5,7,7-trimethylbicyclo[3.3.1]non-2-ene-2-carboxanilide (9).