Ahmad-Strong synthesis of 8-, 9-, and 10-pentadecynoic acids

Three pentadecynoic acids, with the triple bond in the 8-, 9-, and 10-positions, have been synthesized on a gram scale in over-all yield of 65% by refinements of the five-step Ahmad-Strong method; isolation of intermediates was shown to be unnecessary prior to purification of the acetylenic nitriles...

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Bibliographic Details
Main Authors: David R. Howton, Robert A. Stein
Format: Article
Language:English
Published: Elsevier 1969-11-01
Series:Journal of Lipid Research
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S0022227520430226
Description
Summary:Three pentadecynoic acids, with the triple bond in the 8-, 9-, and 10-positions, have been synthesized on a gram scale in over-all yield of 65% by refinements of the five-step Ahmad-Strong method; isolation of intermediates was shown to be unnecessary prior to purification of the acetylenic nitriles by column chromatography on silicic acid.The melting points of the pentadecynoic acids alternate regularly and widely with position of unsaturation, in marked contrast to behavior of the homologous octadecynoic acids described by Huber.
ISSN:0022-2275