Various methods of synthesizing the novel, highly congested bis(tris(trimethylsilyl)methyl) disulfide (2) were investigated. / It was found that the oxidation of tris(trimethylsilyl)methyl mercaptan (1) with iodine in the presence of sodium methoxide affords a product whose $ sp{13}$C, $ sp1$H and combustion data are consistent with its structure being that of 2. In another attempt at the preparation of 2, tris(trimethylsilyl) methane with methyl lithium, elemental sulfur and iodine gave rise to 2 unanticipated products, believed to be bis(trimethylsilyl)methyl, tris(trimethylsilyl)methyl disulfide (3a) and bis(tris(trimethylsilyl)methyl) trisulfide (3c). / Furthermore, trisulfide 3c was subsequently prepared by the sulfuration of 1 using SCl$ sb2$ or N,N-thiobisbenzimidazole. In addition to thiol 1, both 3c and 2 exhibited unanticipated multiplicity of $ sp{13}$C NMR peaks in the silyl region of the spectrum. As a result, efforts were made to explain these results by molecular mechanics calculations on the thiol, trisulfide and disulfide structures.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.59552 |
| Date | January 1990 |
| Creators | Maher, Denise C. (Denise Christine) |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Master of Science (Department of Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 001072928, proquestno: AAIMM63693, Theses scanned by UMI/ProQuest. |
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