The synthesis and benzannulation reactions of (trialkylsilyl)vinylketenes
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, February 2008.
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| Format: | Disertacija |
| Jezik: | eng |
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Massachusetts Institute of Technology
2008
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| Online pristup: | http://hdl.handle.net/1721.1/43086 |
| _version_ | 1826208606445371392 |
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| author | Austin, Wesley F |
| author2 | Rick L. Danheiser. |
| author_facet | Rick L. Danheiser. Austin, Wesley F |
| author_sort | Austin, Wesley F |
| collection | MIT |
| description | Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, February 2008. |
| first_indexed | 2024-09-23T14:08:17Z |
| format | Thesis |
| id | mit-1721.1/43086 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T14:08:17Z |
| publishDate | 2008 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/430862019-04-11T03:43:25Z The synthesis and benzannulation reactions of (trialkylsilyl)vinylketenes Austin, Wesley F Rick L. Danheiser. Massachusetts Institute of Technology. Dept. of Chemistry. Massachusetts Institute of Technology. Dept. of Chemistry. Chemistry. Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, February 2008. Vita. Includes bibliographical references. (Trialkylsilyl)vinylketenes ("TAS-vinylketenes") are versatile four-carbon building blocks in a variety of methods for the synthesis of carbocyclic and heterocyclic compounds. This thesis discusses the development of a new benzannulation strategy for the synthesis of phenols based on the reaction of TAS-vinylketenes with lithium ynolates. Studies have shown that the reaction proceeds by formation and electrocyclic ring closure of 3-oxidodienylketene intermediates, followed by an intramolecular 1,3-silyl migration to provide highly substituted 3-siloxy phenols. Further transformations of these products providing efficient access to ortho-benzoquinones and benzofuran, benzoxepine, and benzoxocine ring systems are described. Additionally, unsuccessful attempts to prepare TAS-vinylketenes by the rearrangement of siloxy alkynes and by cross-metathesis are discussed. by Wesley F. Austin. Ph.D. 2008-11-07T19:00:34Z 2008-11-07T19:00:34Z 2007 2008 Thesis http://hdl.handle.net/1721.1/43086 244391326 eng M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission. http://dspace.mit.edu/handle/1721.1/7582 244 [2] p. application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Austin, Wesley F The synthesis and benzannulation reactions of (trialkylsilyl)vinylketenes |
| title | The synthesis and benzannulation reactions of (trialkylsilyl)vinylketenes |
| title_full | The synthesis and benzannulation reactions of (trialkylsilyl)vinylketenes |
| title_fullStr | The synthesis and benzannulation reactions of (trialkylsilyl)vinylketenes |
| title_full_unstemmed | The synthesis and benzannulation reactions of (trialkylsilyl)vinylketenes |
| title_short | The synthesis and benzannulation reactions of (trialkylsilyl)vinylketenes |
| title_sort | synthesis and benzannulation reactions of trialkylsilyl vinylketenes |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/43086 |
| work_keys_str_mv | AT austinwesleyf thesynthesisandbenzannulationreactionsoftrialkylsilylvinylketenes AT austinwesleyf synthesisandbenzannulationreactionsoftrialkylsilylvinylketenes |