| Summary: | Electrosynthetic methods are of growing contemporary interest, due to the unique reactivity that they can facilitate, and their potential for improved sustainability compared to conventional methods. This thesis discusses the development of two different electrosynthetic reactions.
We disclose the electrochemical deoxygenation of benzylic alcohols using an electrochemically-generated phosphine radical cation. The scope and functional group tolerance of the chemistry is explored, and yields of up to 98% were achieved. The deoxygenation is specific to benzylic alcohols, and chemical, electrochemical and computational investigations provide insight into the operative mechanism of the transformation. Additionally, attempts to develop an electrochemical dehydroxylative functionalisation reaction are briefly discussed.
The development of an electrochemical route to spirocycles from β-hydroxyacids is outlined, and the scope and functional group tolerance of the chemistry is explored. The reaction was carried out in flow, achieving a yield of 43% under unoptimised conditions.
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