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

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:
acetylenic
carboxylic acids
nitriles
polymethylene halides
dimethyl sulfoxide
gas chromatography
Online Access:http://www.sciencedirect.com/science/article/pii/S0022227520430226
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spelling doaj-278704d455c54133b2c0982a9f857f1f2021-04-24T05:55:06ZengElsevierJournal of Lipid Research0022-22751969-11-01106631635Ahmad-Strong synthesis of 8-, 9-, and 10-pentadecynoic acidsDavid R. Howton0Robert A. Stein1Laboratory of Nuclear Medicine and Radiation Biology, University of California, Los Angeles, California 90024; Departments of Biophysics and Biological Chemistry, University of California at Los Angeles, School of Medicine, Los Angeles, California 90024Laboratory of Nuclear Medicine and Radiation Biology, University of California, Los Angeles, California 90024; Departments of Biophysics and Biological Chemistry, University of California at Los Angeles, School of Medicine, Los Angeles, California 90024Three 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.http://www.sciencedirect.com/science/article/pii/S0022227520430226acetyleniccarboxylic acidsnitrilespolymethylene halidesdimethyl sulfoxidegas chromatography
collection DOAJ
language English
format Article
sources DOAJ
author David R. Howton
Robert A. Stein
spellingShingle David R. Howton
Robert A. Stein
Ahmad-Strong synthesis of 8-, 9-, and 10-pentadecynoic acids
Journal of Lipid Research
acetylenic
carboxylic acids
nitriles
polymethylene halides
dimethyl sulfoxide
gas chromatography
author_facet David R. Howton
Robert A. Stein
author_sort David R. Howton
title Ahmad-Strong synthesis of 8-, 9-, and 10-pentadecynoic acids
title_short Ahmad-Strong synthesis of 8-, 9-, and 10-pentadecynoic acids
title_full Ahmad-Strong synthesis of 8-, 9-, and 10-pentadecynoic acids
title_fullStr Ahmad-Strong synthesis of 8-, 9-, and 10-pentadecynoic acids
title_full_unstemmed Ahmad-Strong synthesis of 8-, 9-, and 10-pentadecynoic acids
title_sort ahmad-strong synthesis of 8-, 9-, and 10-pentadecynoic acids
publisher Elsevier
series Journal of Lipid Research
issn 0022-2275
publishDate 1969-11-01
description 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.
topic acetylenic
carboxylic acids
nitriles
polymethylene halides
dimethyl sulfoxide
gas chromatography
url http://www.sciencedirect.com/science/article/pii/S0022227520430226
work_keys_str_mv AT davidrhowton ahmadstrongsynthesisof89and10pentadecynoicacids
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