Synthesis of three isomers of linoleic acid

Synthesis of three isomers of linoleic acid

Thesis (Ph.D.)--Boston University === Three skipped unsaturated fatty acids, 8,11-octadecadienoic acid, 10,13-octadecadienoic acid and 11,14-octadecadienoic acid have been synthesized via skipped acetylenic intermediates. Coupling an w-chloroacetylenic Grignard derivative I with a propargylic bromi...

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Main Author: Bruno, John Joseph
Language:en_US
Published: Boston University 2018
Subjects:
Linoleic acid
Octadecadienoic acid
Online Access:https://hdl.handle.net/2144/31348
id ndltd-bu.edu-oai-open.bu.edu-2144-31348
record_format oai_dc
spelling ndltd-bu.edu-oai-open.bu.edu-2144-313482019-01-08T15:44:51Z Synthesis of three isomers of linoleic acid Bruno, John Joseph Linoleic acid Octadecadienoic acid Thesis (Ph.D.)--Boston University Three skipped unsaturated fatty acids, 8,11-octadecadienoic acid, 10,13-octadecadienoic acid and 11,14-octadecadienoic acid have been synthesized via skipped acetylenic intermediates. Coupling an w-chloroacetylenic Grignard derivative I with a propargylic bromide II in tetrahydrofuran in the presence of cuprous chloride catalyst yielded a 1-chloroheptadecadiyne III, which was reduced stereospecifically and selectively to the di-cis-1-chloroheptadecadiene IV by two treatments with diisobutylaluminum hydride. The diene IV was converted to the Grignard reagent which upon carbonation and acidification gave the octadecadienoic acid V[TRUNCATED] 2018-09-27T18:54:30Z 2018-09-27T18:54:30Z 1961 1961 Thesis/Dissertation b14686016 https://hdl.handle.net/2144/31348 11719025203961 99175769060001161 en_US Based on investigation of the BU Libraries' staff, this work is free of known copyright restrictions. Boston University
collection NDLTD
language en_US
sources NDLTD
topic Linoleic acid
Octadecadienoic acid
spellingShingle Linoleic acid
Octadecadienoic acid
Bruno, John Joseph
Synthesis of three isomers of linoleic acid
description Thesis (Ph.D.)--Boston University === Three skipped unsaturated fatty acids, 8,11-octadecadienoic acid, 10,13-octadecadienoic acid and 11,14-octadecadienoic acid have been synthesized via skipped acetylenic intermediates. Coupling an w-chloroacetylenic Grignard derivative I with a propargylic bromide II in tetrahydrofuran in the presence of cuprous chloride catalyst yielded a 1-chloroheptadecadiyne III, which was reduced stereospecifically and selectively to the di-cis-1-chloroheptadecadiene IV by two treatments with diisobutylaluminum hydride. The diene IV was converted to the Grignard reagent which upon carbonation and acidification gave the octadecadienoic acid V[TRUNCATED]
author Bruno, John Joseph
author_facet Bruno, John Joseph
author_sort Bruno, John Joseph
title Synthesis of three isomers of linoleic acid
title_short Synthesis of three isomers of linoleic acid
title_full Synthesis of three isomers of linoleic acid
title_fullStr Synthesis of three isomers of linoleic acid
title_full_unstemmed Synthesis of three isomers of linoleic acid
title_sort synthesis of three isomers of linoleic acid
publisher Boston University
publishDate 2018
url https://hdl.handle.net/2144/31348
work_keys_str_mv AT brunojohnjoseph synthesisofthreeisomersoflinoleicacid
_version_ 1718813021602578432

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