Isolable spirocyclic silylone: π-delocalized spiro[3.3]heptasila-2,6-diylidone
Strained cyclic tetrylones are important synthons due to various synthetic applications. Connecting two cyclic tetrylone rings through a single shared quaternary group 14 element atom to form a spirocyclic molecule has been unexplored both theoretically and experimentally. The formation of a spirocy...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2024
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| Online Access: | https://hdl.handle.net/10356/179284 |
| _version_ | 1826110643017613312 |
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| author | Wee, Meldon Yi-Shuo Quek, Shina Wu, Chi-Shiun Su, Ming-Der So, Cheuk-Wai |
| author2 | School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet | School of Chemistry, Chemical Engineering and Biotechnology Wee, Meldon Yi-Shuo Quek, Shina Wu, Chi-Shiun Su, Ming-Der So, Cheuk-Wai |
| author_sort | Wee, Meldon Yi-Shuo |
| collection | NTU |
| description | Strained cyclic tetrylones are important synthons due to various synthetic applications. Connecting two cyclic tetrylone rings through a single shared quaternary group 14 element atom to form a spirocyclic molecule has been unexplored both theoretically and experimentally. The formation of a spirocyclic motif has been a synthetic challenge. In contrast, the reaction of amidinato disilicon(I) 1, (Me3P)2SiCl4, and KC8 afforded π-delocalized spiro[3.3]heptasila-2,6-diylidone2 and tetrasilacyclobutadiene byproducts 3 and 4. Compound 2 is the smallest spirocyclic tetrylone derivative, which is composed of a σ-type lone pair and delocalized π bond in each all-silicon spirocyclic ring. The electronic property is supported by its coordination with a W(CO)5 moiety. |
| first_indexed | 2024-10-01T02:37:51Z |
| format | Journal Article |
| id | ntu-10356/179284 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T02:37:51Z |
| publishDate | 2024 |
| record_format | dspace |
| spelling | ntu-10356/1792842024-07-24T07:54:30Z Isolable spirocyclic silylone: π-delocalized spiro[3.3]heptasila-2,6-diylidone Wee, Meldon Yi-Shuo Quek, Shina Wu, Chi-Shiun Su, Ming-Der So, Cheuk-Wai School of Chemistry, Chemical Engineering and Biotechnology Chemistry Spirocyclic silylone Spironolactone Strained cyclic tetrylones are important synthons due to various synthetic applications. Connecting two cyclic tetrylone rings through a single shared quaternary group 14 element atom to form a spirocyclic molecule has been unexplored both theoretically and experimentally. The formation of a spirocyclic motif has been a synthetic challenge. In contrast, the reaction of amidinato disilicon(I) 1, (Me3P)2SiCl4, and KC8 afforded π-delocalized spiro[3.3]heptasila-2,6-diylidone2 and tetrasilacyclobutadiene byproducts 3 and 4. Compound 2 is the smallest spirocyclic tetrylone derivative, which is composed of a σ-type lone pair and delocalized π bond in each all-silicon spirocyclic ring. The electronic property is supported by its coordination with a W(CO)5 moiety. Agency for Science, Technology and Research (A*STAR) Ministry of Education (MOE) This work was supported by the Ministry of Education Singapore, AcRF Tier 2 (MOE2019-T2-2-129) and A*STAR MTC Individual Research Grants (M21K2c0117) for financial support (C.-W.S.). C.-S.W. and M.-D.S. acknowledge the National Center for High-Performance Computing of Taiwan for generous amounts of computing time and the Ministry of Science and Technology of Taiwan for financial support. 2024-07-24T07:54:30Z 2024-07-24T07:54:30Z 2024 Journal Article Wee, M. Y., Quek, S., Wu, C., Su, M. & So, C. (2024). Isolable spirocyclic silylone: π-delocalized spiro[3.3]heptasila-2,6-diylidone. Journal of the American Chemical Society, 146(21), 14410-14415. https://dx.doi.org/10.1021/jacs.4c02807 0002-7863 https://hdl.handle.net/10356/179284 10.1021/jacs.4c02807 38754079 2-s2.0-85193604320 21 146 14410 14415 en MOE2019-T2-2-129 M21K2c0117 Journal of the American Chemical Society © 2024 American Chemical Society. All rights reserved. |
| spellingShingle | Chemistry Spirocyclic silylone Spironolactone Wee, Meldon Yi-Shuo Quek, Shina Wu, Chi-Shiun Su, Ming-Der So, Cheuk-Wai Isolable spirocyclic silylone: π-delocalized spiro[3.3]heptasila-2,6-diylidone |
| title | Isolable spirocyclic silylone: π-delocalized spiro[3.3]heptasila-2,6-diylidone |
| title_full | Isolable spirocyclic silylone: π-delocalized spiro[3.3]heptasila-2,6-diylidone |
| title_fullStr | Isolable spirocyclic silylone: π-delocalized spiro[3.3]heptasila-2,6-diylidone |
| title_full_unstemmed | Isolable spirocyclic silylone: π-delocalized spiro[3.3]heptasila-2,6-diylidone |
| title_short | Isolable spirocyclic silylone: π-delocalized spiro[3.3]heptasila-2,6-diylidone |
| title_sort | isolable spirocyclic silylone π delocalized spiro 3 3 heptasila 2 6 diylidone |
| topic | Chemistry Spirocyclic silylone Spironolactone |
| url | https://hdl.handle.net/10356/179284 |
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