Tin-free radical mediated C-C bond formation via the Xanthate transfer
Formation of carbon-carbon bonds had been by far the most researched and refined objective in organic synthesis. On the contrary, the use of free-radical chemistry in this area had thus been limited to tin-mediated protocols which were gradually losing popularity due to toxicity and purification iss...
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| Format: | Thesis |
| Language: | English |
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2015
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| Online Access: | https://hdl.handle.net/10356/62948 |
| _version_ | 1826120109151748096 |
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| author | Goh, Kelvin Kau Kiat |
| author2 | Loh Teck Peng |
| author_facet | Loh Teck Peng Goh, Kelvin Kau Kiat |
| author_sort | Goh, Kelvin Kau Kiat |
| collection | NTU |
| description | Formation of carbon-carbon bonds had been by far the most researched and refined objective in organic synthesis. On the contrary, the use of free-radical chemistry in this area had thus been limited to tin-mediated protocols which were gradually losing popularity due to toxicity and purification issues. Xanthates, a class of thiocarbonylthio compounds have found remarkable application in both inter- and intra-molecular tin-free radical additions to simple and un-activated olefins. In this thesis, the use of xanthates is further explored and renewed through combination with other types of radical chemistry previously employed with tin-based initiators. The goal is to develop novel tin-free solutions in the C-C bond formation for the synthesis of highly functionalized molecules which had otherwise been plagued by acid-base problems in ionic chemistry. This concept is briefly demonstrated by a few free-radical alternatives to enolate chemistry involving ketones, lactones and thiolactones. |
| first_indexed | 2024-10-01T05:11:08Z |
| format | Thesis |
| id | ntu-10356/62948 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:11:08Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/629482023-02-28T23:44:39Z Tin-free radical mediated C-C bond formation via the Xanthate transfer Goh, Kelvin Kau Kiat Loh Teck Peng School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Formation of carbon-carbon bonds had been by far the most researched and refined objective in organic synthesis. On the contrary, the use of free-radical chemistry in this area had thus been limited to tin-mediated protocols which were gradually losing popularity due to toxicity and purification issues. Xanthates, a class of thiocarbonylthio compounds have found remarkable application in both inter- and intra-molecular tin-free radical additions to simple and un-activated olefins. In this thesis, the use of xanthates is further explored and renewed through combination with other types of radical chemistry previously employed with tin-based initiators. The goal is to develop novel tin-free solutions in the C-C bond formation for the synthesis of highly functionalized molecules which had otherwise been plagued by acid-base problems in ionic chemistry. This concept is briefly demonstrated by a few free-radical alternatives to enolate chemistry involving ketones, lactones and thiolactones. DOCTOR OF PHILOSOPHY (SPMS) 2015-05-04T04:42:57Z 2015-05-04T04:42:57Z 2015 2015 Thesis Goh, K. K. K. (2015). Tin-free radical mediated C-C bond formation via the Xanthate transfer. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/62948 10.32657/10356/62948 en 595 p. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Goh, Kelvin Kau Kiat Tin-free radical mediated C-C bond formation via the Xanthate transfer |
| title | Tin-free radical mediated C-C bond formation via the Xanthate transfer |
| title_full | Tin-free radical mediated C-C bond formation via the Xanthate transfer |
| title_fullStr | Tin-free radical mediated C-C bond formation via the Xanthate transfer |
| title_full_unstemmed | Tin-free radical mediated C-C bond formation via the Xanthate transfer |
| title_short | Tin-free radical mediated C-C bond formation via the Xanthate transfer |
| title_sort | tin free radical mediated c c bond formation via the xanthate transfer |
| topic | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis |
| url | https://hdl.handle.net/10356/62948 |
| work_keys_str_mv | AT gohkelvinkaukiat tinfreeradicalmediatedccbondformationviathexanthatetransfer |