2026-09-19T11:28:41.138673600Zhttps://opus.uleth.ca/server/oai/request
oai:opus.uleth.ca:10133/62512022-06-24T06:05:27Zcom_10133_3346com_10133_1com_10133_296col_10133_3347col_10133_298
ULethbridge OPUS Repository supervisor Hayes, Paul G. author Webb, Dylan James author University of Lethbridge. Faculty of Arts and Science 2022-06-23T22:22:20Z 2022-06-23T22:22:20Z 2022 https://hdl.handle.net/10133/6251 Part I describes the synthesis of neutral bis(phosphinimine) NEN-pincer ligands. The ligands vary at the neutral central donor, E, the flanking aromatic group, and P-substituents. Cationic alkyl and phenoxide zinc complexes of this ligand system were synthesized to understand the steric and electronic factors that govern the complexes capacity to serve as catalysts for the ring-opening polymerization of ε-caprolactone. Part II describes the semisynthetic strategies for the generation of the major cannabinoids (9THC and CBD), and the lower abundant cannabinoids 8THC and CBN. Lesser-known cannabinoids and related derivatives were also prepared. Their in vitro chemotherapeutic action to breast cancer cells is described, attempting to decipher a relationship to chemical structure. Other investigations include computational analysis and reduction of the ortho-quinoids. A quantitative NMR procedure was used to determine purity of cannabinoids extracted. Compounds were characterized via multi-dimensional and multi-nuclear NMR spectroscopy, elemental analysis, and, where possible, single-crystal X-ray diffraction experiments. en_US coordination chemistry organic synthesis polymer chemistry Organic compounds--Synthesis Coordination compounds Polymerization Cannabinoids--Synthesis Cannabinoids--Derivatives Ligands Dissertations, Academic I. Synthesis and ring-opening polymerization of cationic divalent metal complexes supported by NEN-pincer ligands (E = O, S, Se); II. Semisynthesis strategies for the generation of cannabinoids and related derivatives Thesis 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 URL http://localhost:4000/bitstreams/55bc864a-067f-4614-95af-1d72ed7737b8/download File MD5 0f6049e6b00c578577e2777999c5f439 11616100 application/pdf WEBB_DYLAN_PHD_2022.pdf URL http://localhost:4000/bitstreams/ac2c1ff8-f47c-4112-8983-2318bba0be32/download File MD5 560fc9febc4fa111f6196281a782586f 520122 text/plain WEBB_DYLAN_PHD_2022.pdf.txt