Oxidative cyclization of unsaturated fatty acids with lead tetraacetate

The reaction of 10-undecenoic acid with lead tetraacetate (LTA) in the presence of acetic acid and anhydrous potassium acetate gave a eutectic mixture of 10(11)-acetoxy-11(10)-methylundecanoic acid (25%), 10,11-diacetoxyundecanoic acid (15%) and 5-(ω-carboxyoctyl) γ-butyrolactone (45%). Similar reaction withcis-9-octadecenoic acid yielded a eutectic mixture of 9(10)-acetoxy-10(9)-methyloctadecanoic acid (20%) and 4(5)-(ω-carboxyheptyl)-5-(4)-octyl γ-butyrolactone (40%). In the reaction withtrans-2-enoic acids (C₁₆ and C₁₈) products obtained were: 1,2-diacetoxypenta- and heptadecane (27%), 3-acetoxyhexa- and octadecanoic acid (31%) and 2-(2-penta- and heptadecyl) succinic anhydride (23%), respectively. The structures of individual compounds were characterized by spectral methods.