Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes
Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2012.
| Main Author: | |
|---|---|
| Other Authors: | |
| Format: | Thesis |
| Language: | eng |
| Published: |
Massachusetts Institute of Technology
2012
|
| Subjects: | |
| Online Access: | http://hdl.handle.net/1721.1/73390 |
| _version_ | 1826191327526649856 |
|---|---|
| author | Aguirre Kohnen, Amanda L. (Amanda Lucille) |
| author2 | Rick L. Danheiser. |
| author_facet | Rick L. Danheiser. Aguirre Kohnen, Amanda L. (Amanda Lucille) |
| author_sort | Aguirre Kohnen, Amanda L. (Amanda Lucille) |
| collection | MIT |
| description | Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2012. |
| first_indexed | 2024-09-23T08:54:11Z |
| format | Thesis |
| id | mit-1721.1/73390 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T08:54:11Z |
| publishDate | 2012 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/733902019-04-10T17:07:13Z Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes Aguirre Kohnen, Amanda L. (Amanda Lucille) Rick L. Danheiser. Massachusetts Institute of Technology. Dept. of Chemistry. Massachusetts Institute of Technology. Dept. of Chemistry. Chemistry. Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2012. Cataloged from PDF version of thesis. Includes bibliographical references. Ynamides react with various classes of ketenes in intermolecular [2 + 2] cycloaddition to afford substituted cyclobutenones with complete regioselectivity. The cycloaddition substrates are easily assembled from amine derivatives by copper-catalyzed N-alkynylation with acetylenic bromides. The alkynylation reaction provides access to thermally sensitive compounds such as diynamides. Synthesis of the requisite halo diynes is achieved by Sonogashira coupling followed by base-mediated elimination at low temperature. by Amanda L. Aguirre Kohnen. S.M. 2012-09-27T15:28:10Z 2012-09-27T15:28:10Z 2012 2012 Thesis http://hdl.handle.net/1721.1/73390 809806329 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 57 p. application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Aguirre Kohnen, Amanda L. (Amanda Lucille) Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes |
| title | Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes |
| title_full | Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes |
| title_fullStr | Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes |
| title_full_unstemmed | Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes |
| title_short | Synthesis of 3-aminocyclobutenones via [2 + 2] cycloaddition of ynamides and ketenes |
| title_sort | synthesis of 3 aminocyclobutenones via 2 2 cycloaddition of ynamides and ketenes |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/73390 |
| work_keys_str_mv | AT aguirrekohnenamandalamandalucille synthesisof3aminocyclobutenonesvia22cycloadditionofynamidesandketenes |