Oxidative Bromination and Ring Expansion in Organic Chemistry

This thesis is composed of two independent research projects. The first major project discussed is electrophilic halogenation using inorganic halides in the presence of oxidant. This includes the conversion of tertiary propargyl alcohols in to α,α-dihaloketones.
In addition, the oxidative bromination of a range of alkylbenzene derivatives using the inexpensive
oxidant Oxone and sodium bromide is described with up to 4 C-H bonds being functionalised in
this process.
The second part of this thesis focuses on using silacyclobutanes in our aim to access new siliconcontaining chemical space. Silacyclobutanes are useful in organic synthesis because of their exciting reactivity based on their high Lewis acidity and ring strain. We describe our efforts at developing catalytic conditions for the Pd-mediated dimerisation of silacyclobutanes, as well as our preliminary results on the nickel-catalysed enantioselective ring expansion of benzosilacyclobutane with aldehydes. After Tamao-Fleming oxidation, this reaction produces extremely useful chiral benzylic alcohols.