Date of Award
2004
Publication Type
Master Thesis
Degree Name
M.Sc.
Department
Chemistry and Biochemistry
Keywords
Chemistry, Organic.
Rights
info:eu-repo/semantics/openAccess
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 4.0 International License.
Abstract
There are several naturally occurring compounds that have fused 7,5-bicyclic ring systems. This thesis will focus on approaches to synthesizing 7,5-bicyclic systems containing a dicobalt hexacarbonyl complex. In this context, the allylic acetate cycloheptenyne complex (66) was reacted with various carbon- and hetero-based nucleophiles to determine the regiochemistry of the substitution. The gamma to alpha ratio for carbon-based nucleophiles were approximately 4:1, while hetero-based nucleophiles were 100% gamma. Once the ratios were established, several of these product compounds, which contained an electrophilic site, were investigated for further reaction to form the additional ring (Scheme 28). Formation of a 7,5-bicyclic ketone 131, alcohol 132 and diol 133 were observed when compound 129 was mixed with boron trifluoride (Scheme 42).Dept. of Chemistry and Biochemistry. Paper copy at Leddy Library: Theses & Major Papers - Basement, West Bldg. / Call Number: Thesis2004 .D56. Source: Masters Abstracts International, Volume: 43-01, page: 0218. Thesis (M.Sc.)--University of Windsor (Canada), 2004.
Recommended Citation
DiMartino, Joseph, "Regiochemical studies for nucleophilic addition on allylic acetate cycloheptyne cobalt complexes and the progression towards the synthesis of 7,5-bicyclic ring systems containing the cobalt complex." (2004). Electronic Theses and Dissertations. 3295.
https://scholar.uwindsor.ca/etd/3295
