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Oxidative cyclization of unsaturated fatty acids with lead tetraacetate
Author(s) -
Hashmi M.,
Khan M.,
Ahmad M. S.,
Ahmad F.,
Osman S. M.
Publication year - 1983
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02666579
Subject(s) - chemistry , succinic acid , anhydrous , acetic anhydride , succinic anhydride , acetic acid , organic chemistry , eutectic system , fatty acid , potassium carbonate , medicinal chemistry , catalysis , alloy
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 with cis ‐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 with trans ‐2‐enoic acids (C 16 and C 18 ) 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.