Metal-Catalyzed Organic Photoreactions. Bond-Cleavage Selectivity and Synthetic Application of the Iron(III) Chloride Catalyzed Photooxidation of Cyclic Olefins

Article abstract of DOI:10.1021/jo00152a004

Photooxidation of olefins in pyridine in the presence of iron(III) chloride produced either α-chloro ketones (type A), gem-dichloro ketones (type B), or α,ω-dichloro ketones (type C), depending upon the substitution pattern of the substrate olefin.The synthetic utility of the type B reaction was demonstrated by the synthesis of some natural products.The synthesis of optically active solanone from D-p-menthene confirmed the D configuration of the natural product.