Oxidative cyclization of unsaturated fatty acids with lead tetraacetate | Zendy

Hashmi M. | Zendy; Khan M. | Zendy; Ahmad M. S. | Zendy; Ahmad F. | Zendy; Osman S. M. | Zendy

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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.

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