Studies on Allylic Oxidation of Carotenoids.

Abstract
Catalysis by iodine and light of the aerobic oxidation of carotenoids containing allylic hydroxyl groups to the corresponding ketones is reported. Molecular oxygen (air) can with advantage be replaced by p- chloranil as oxidant, and the catalytic effect of iodine and light on the allylic oxidation with p-chloranil is demonstrated. Illumination by means of standardized artificial light is the method of choice. On exposure to artificial Na-light the production of undesirable side-products was suppressed, and a nearly quantitative yield of keto-products was obtained. The method has been employed for the partial synthesis of 4-hydroxy-4[image]-keto-[beta]-carotene (IV) from isozeaxanthin (III), and compound (IV) has been characterized.