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Syntheses of cis‐ and trans‐7‐ and 8‐octadecenoic acids: Comparison of the properties of cis‐ and trans‐6‐, 7‐, 8‐, 9‐, and 11‐octadecenoic acids
Author(s) -
Fusari Salvatore A.,
Greenlee K. W.,
Brown J. B.
Publication year - 1951
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/bf02589677
Subject(s) - cis–trans isomerism , chemistry , organic chemistry , stereochemistry , medicinal chemistry
Summary 1. The cis‐ and trans‐modifications of 7‐, 8‐, and 11‐octadecenoic acids were synthesized by methods which leave no doubt as to their structure. 2. Many new compounds have been reported including 7‐octadecynoic acid, 8‐octadecynoic acid. 7,8‐diketostearic acid, 8,9‐diketostearic acid, cis‐ and trans‐7‐octadecenoic acids and their 7,8‐dihydroxystearic acid derivatives, and cis‐ and trans‐8‐octadecenoic acid derivatives and their 8,9‐dihydroxystearic acid derivatives. 3. A new series of intermediate reaction products has been reported although these compounds were not fully characterized. These compounds include hexamethylene bromochloride, hexamethylene iodochloride, 1‐chloro‐6‐heptadecyne, and 1‐chloro‐7‐heptadecyne. 4. The extinction coefficients at 10.36 microns of the cis and trans‐6‐, 7‐, 8‐, 9‐, and 11‐octadecenoic acids have been calculated and compared. 5. The melting points of the cis‐ and trans‐octadecenoic acids and their dihydroxy derivatives were shown to exhibit alternating patterns.