Electrochemical Deoxygenation of Benzylic Alcohols and Electrosynthesis of Spirocycles
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 t...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
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2024
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| Online Access: | https://eprints.nottingham.ac.uk/78215/ |
| _version_ | 1848801059316695040 |
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| author | Edmonds, Alex |
| author_facet | Edmonds, Alex |
| author_sort | Edmonds, Alex |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T21:01:26Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-78215 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:01:26Z |
| publishDate | 2024 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-782152025-02-28T15:20:58Z https://eprints.nottingham.ac.uk/78215/ Electrochemical Deoxygenation of Benzylic Alcohols and Electrosynthesis of Spirocycles Edmonds, Alex 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. 2024-07-24 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en cc_by https://eprints.nottingham.ac.uk/78215/1/Edmonds%2C%20Alex%2C%2014255927%2C%20Corrected%20Thesis.pdf Edmonds, Alex (2024) Electrochemical Deoxygenation of Benzylic Alcohols and Electrosynthesis of Spirocycles. PhD thesis, University of Nottingham. Electrochemistry Electrosynthesis Deoxygenation Phosphoranyl Radical Semipinacol Rearrangement Spirocycles |
| spellingShingle | Electrochemistry Electrosynthesis Deoxygenation Phosphoranyl Radical Semipinacol Rearrangement Spirocycles Edmonds, Alex Electrochemical Deoxygenation of Benzylic Alcohols and Electrosynthesis of Spirocycles |
| title | Electrochemical Deoxygenation of Benzylic Alcohols and Electrosynthesis of Spirocycles |
| title_full | Electrochemical Deoxygenation of Benzylic Alcohols and Electrosynthesis of Spirocycles |
| title_fullStr | Electrochemical Deoxygenation of Benzylic Alcohols and Electrosynthesis of Spirocycles |
| title_full_unstemmed | Electrochemical Deoxygenation of Benzylic Alcohols and Electrosynthesis of Spirocycles |
| title_short | Electrochemical Deoxygenation of Benzylic Alcohols and Electrosynthesis of Spirocycles |
| title_sort | electrochemical deoxygenation of benzylic alcohols and electrosynthesis of spirocycles |
| topic | Electrochemistry Electrosynthesis Deoxygenation Phosphoranyl Radical Semipinacol Rearrangement Spirocycles |
| url | https://eprints.nottingham.ac.uk/78215/ |