Reactions of conjugated fatty acids. VI. Selenium catalysis, a method for preparing diels‐alder adducts from cis,trans‐octadecadienoic acid | Zendy

Teeter H. M. | Zendy; Bell E. W. | Zendy; O'Donnell J. L. | Zendy; Danzig M. J. | Zendy; Cowan J. C. | Zendy

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Reactions of conjugated fatty acids. VI. Selenium catalysis, a method for preparing diels‐alder adducts from cis,trans‐octadecadienoic acid

Author(s) -

Teeter H. M.,

Bell E. W.,

O'Donnell J. L.,

Danzig M. J.,

Cowan J. C.

Publication year - 1958

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/bf02639835

Subject(s) - chemistry , peracetic acid , catalysis , isomerization , yield (engineering) , adduct , conjugated linoleic acid , selenium , organic chemistry , conjugated system , linoleic acid , hydrogen peroxide , polyunsaturated fatty acid , fatty acid , medicinal chemistry , polymer , materials science , metallurgy

Summary Adducts of dienophiles and alkali‐conjugated safflower fatty acids containing conjugated linoleic acid in the cis,trans form were prepared by heating the reactants in the presence of selenium as a catalyst. The products appeared to be identical to those prepared from trans,trans conjugated linoleic acid so that isomerization of cis‐trans to trans,trans acids is eliminated as a separate step. Although yields of pure product were lower than desired because of difficulties in removing selenium, yields of crude adducts ranged from 64–82%. The adducts obtained could be epoxidized with hydrogen peroxide and an ion‐exchange resin as catalyst in 80–93% yield or with peracetic acid in 89–98% yield.

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