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]
| Identifer | oai:union.ndltd.org:bu.edu/oai:open.bu.edu:2144/31348 |
| Date | January 1961 |
| Creators | Bruno, John Joseph |
| Publisher | Boston University |
| Source Sets | Boston University |
| Language | en_US |
| Detected Language | English |
| Type | Thesis/Dissertation |
| Rights | Based on investigation of the BU Libraries' staff, this work is free of known copyright restrictions. |
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