PHOTODIMERIC CAGE COMPOUNDS .V. TRANSFORMATIONS OF DIOXIMES OF PHOTODIMERS OF 2,6-DIMETHYL- AND 2,6-DIETHYL-4-PYRONE

Treatment of the dioxime (3) of the cage photodimer of 2,6-dimethyl-4-pyrone with concentrated sulfuric acid gives [3-(5-methylisoxazyl]acetone (5), the oxime of 2,6-dimethyl-4-pyrone (12), and l,3-dimethyl-2,4-bis-[3-(5-methylisoxazyl)]-l,3-cyclobutanediol (22). Catalytic hydrogenation of the cyclobutanediol gives 4-amino-4-{3-[6-(2-hydroxypropyl)-2,4-dimethylpyridyl] } -3-buten-2-one (30). Treatment of the dioxime 3 with polyphosphoric acid gives 3,4,6-trimethyl-5-[3-(5-methylisoxazyl)]anthranil (46), in addition to 5 and 22. Treatment of the dioxime (4) of the cage photodimer of 2,6-diethyl-4-pyrone with either concentrated sulfuric acid or polyphosphoric acid gives products analogous to 5 and 12 together with the dioxime of the seco dimer, formed by simple cleavage of one of the cyclobutane rings of the cage. © 1969, American Chemical Society. All rights reserved.