The two naturally occurring cyclopropene fatty acids, sterculic
and malvalic, have been synthesized. The cyclopropene ring was
made by inserting a methylene unit into an acetylenic linkage.
The synthesis of methyl sterculate was repeated using diethyl
aluminum chloride, diazomethane, and methyl stearolate.
Methyl malvalate was totally synthesized. Diethyl malonate
was condensed with 1, 5-dibromopentane to give 7-bromoheptanoic
acid. 1-Decyne was reacted with 7-bromoheptanoic acid to give
7-heptadecynoic acid. 7-Heptadecynoic acid was esterified with
diazomethane. The cyclopropene ring was generated using diethyl
aluminum chloride and diazomethane.
The reaction worked very well and in most cases the yields
exceeded 50 percent. / Graduation date: 1966
| Identifer | oai:union.ndltd.org:ORGSU/oai:ir.library.oregonstate.edu:1957/26781 |
| Date | 20 August 1965 |
| Creators | Kray, William David |
| Contributors | Engebrecht, Ronald H. |
| Source Sets | Oregon State University |
| Language | en_US |
| Detected Language | English |
| Type | Thesis/Dissertation |
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