Oxidative cyclization of unsaturated fatty acids with lead tetraacetate |
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Authors: | M. Hashmi M. Khan M. S. Ahmad F. Ahmad S. M. Osman |
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Affiliation: | (1) Department of Chemistry, Aligarh Muslim University, 202001 Aligarh, India |
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Abstract: | 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. |
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