Pericyclic and related rearrangements for the synthesis of nitrogen heterocyclic ring systems
<p>The thesis describes synthesis and reactions of allene azides tethered to various functional groups and the application of the discovered cascade transformations towards the synthesis of radianspene J model system.</p> <p>Chapter 1 covers reactions of simple allene azides contai...
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| Format: | Thesis |
| Language: | English |
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2013
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| _version_ | 1826299298725232640 |
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| author | Zhurakovskyi, O |
| author2 | Robertson, J |
| author_facet | Robertson, J Zhurakovskyi, O |
| author_sort | Zhurakovskyi, O |
| collection | OXFORD |
| description | <p>The thesis describes synthesis and reactions of allene azides tethered to various functional groups and the application of the discovered cascade transformations towards the synthesis of radianspene J model system.</p> <p>Chapter 1 covers reactions of simple allene azides containing alkyl and cycloalkyl substituents. Thermal rearrangements of these substrates delivered isocyanides and azadienes via the proposed azatrimethylenemethane (ATMM) intermediates.</p> <p>On the other hand, vinylidenecyclopropanes (VDCPs) gave dramatically different products, as described in Chapter 2. A phenyl-substituted VDCP was transformed into an unstable polycyclic compound by a divinylcyclopropane rearrangement. Chapter 3 discusses allene azides tethered to furan, N-substituted pyrroles, and E- and Z-dienes. Depending on the structure of the starting material, products of formal (3+4)- or (2+3)-cycloaddition were formed.</p> <p>Finally, an application of the discovered cyclisation cascade towards total synthesis is described in Chapter 4. A model system of radianspene J was assembled using a key transannular cycloaddition of a macrocyclic allene.</p> |
| first_indexed | 2024-03-07T04:59:48Z |
| format | Thesis |
| id | oxford-uuid:d7e4bbea-4009-4e7e-838c-46b4bb81bc13 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:59:48Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | oxford-uuid:d7e4bbea-4009-4e7e-838c-46b4bb81bc132022-03-27T08:44:16ZPericyclic and related rearrangements for the synthesis of nitrogen heterocyclic ring systemsThesishttp://purl.org/coar/resource_type/c_db06uuid:d7e4bbea-4009-4e7e-838c-46b4bb81bc13Heterocyclic chemistryOrganic synthesisOrganic chemistryNatural productsEnglishOxford University Research Archive - Valet2013Zhurakovskyi, ORobertson, J<p>The thesis describes synthesis and reactions of allene azides tethered to various functional groups and the application of the discovered cascade transformations towards the synthesis of radianspene J model system.</p> <p>Chapter 1 covers reactions of simple allene azides containing alkyl and cycloalkyl substituents. Thermal rearrangements of these substrates delivered isocyanides and azadienes via the proposed azatrimethylenemethane (ATMM) intermediates.</p> <p>On the other hand, vinylidenecyclopropanes (VDCPs) gave dramatically different products, as described in Chapter 2. A phenyl-substituted VDCP was transformed into an unstable polycyclic compound by a divinylcyclopropane rearrangement. Chapter 3 discusses allene azides tethered to furan, N-substituted pyrroles, and E- and Z-dienes. Depending on the structure of the starting material, products of formal (3+4)- or (2+3)-cycloaddition were formed.</p> <p>Finally, an application of the discovered cyclisation cascade towards total synthesis is described in Chapter 4. A model system of radianspene J was assembled using a key transannular cycloaddition of a macrocyclic allene.</p> |
| spellingShingle | Heterocyclic chemistry Organic synthesis Organic chemistry Natural products Zhurakovskyi, O Pericyclic and related rearrangements for the synthesis of nitrogen heterocyclic ring systems |
| title | Pericyclic and related rearrangements for the synthesis of nitrogen heterocyclic ring systems |
| title_full | Pericyclic and related rearrangements for the synthesis of nitrogen heterocyclic ring systems |
| title_fullStr | Pericyclic and related rearrangements for the synthesis of nitrogen heterocyclic ring systems |
| title_full_unstemmed | Pericyclic and related rearrangements for the synthesis of nitrogen heterocyclic ring systems |
| title_short | Pericyclic and related rearrangements for the synthesis of nitrogen heterocyclic ring systems |
| title_sort | pericyclic and related rearrangements for the synthesis of nitrogen heterocyclic ring systems |
| topic | Heterocyclic chemistry Organic synthesis Organic chemistry Natural products |
| work_keys_str_mv | AT zhurakovskyio pericyclicandrelatedrearrangementsforthesynthesisofnitrogenheterocyclicringsystems |