Part I describes an investigation of the following electrophilic substitution reactions of 3-methylfuran. Acylation under Friedel-Crafts conditions yielded 3-methyl-2-acetylfuran (8) and 3-methyl-5-acetylfuran (9) in the ratio 65:35. Vilsmeier and Gatterman formylation procedures yielded 3-methylfurfural (10) and 3-methyl-5-furfural (11) in the same ratio, 93.5:6.5. Mercuration of 3-methylfuran yielded only the 2-mercuro derivative.
Part II describes the isolation and structural elucidation of two major oxygen heterocyclic compounds C and D occurring in the leaves of Zeyhera tuberculosa Bur. et Verlot (Bignoniaceae). Compound C is assigned the structure 5,6,7,8-tetramethoxyflavone (25) on the basis of spectroscopic evidence. Compound D is shown to possess the structure 5,6,7-trimethoxyflavone (35). In this latter instance spectroscopic and chemical evidence could be obtained in support of the structural assignment. In particular, alkaline hydrolysis of D yielded 2,3,4-trimethoxy-6-hydroxyacetophenone (34), the identity of which was established by an unambiguous synthesis.
In the synthesis of the acetophenone derivative (34), the key intermediate is 2,6-dimethoxyhydroquinone diacetate (31) which was subjected to Fries rearrangement conditions, followed by acid hydrolysis, to give 2,4-dimethoxy-3,6-dihydroxyacetophenone (33). Partial methylation of (33) yielded (34). / Science, Faculty of / Chemistry, Department of / Graduate
| Identifer | oai:union.ndltd.org:UBC/oai:circle.library.ubc.ca:2429/34137 |
| Date | January 1970 |
| Creators | Hanssen, Harald Wilhelm |
| Publisher | University of British Columbia |
| Source Sets | University of British Columbia |
| Language | English |
| Detected Language | English |
| Type | Text, Thesis/Dissertation |
| Rights | For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use. |
Page generated in 0.002 seconds