Synthesis of 2-Alkylidenethietanes and the transformation to Thiophenes
During the course of study on the nucleophilic substitution reaction at an sp2 carbon in the Narasaka group, a unique four-membered ring formation was realized by intramolecular nucleophilic vinylic substitution of a thiolate moiety. To generalize this 2-alkylidenethietane formation and to get mo...
| Main Author: | |
|---|---|
| Other Authors: | |
| Format: | Thesis |
| Language: | English |
| Published: |
2009
|
| Subjects: | |
| Online Access: | http://hdl.handle.net/10356/14732 |
| _version_ | 1826116102809190400 |
|---|---|
| author | Xiao, Yongjun |
| author2 | Narasaka, Koichi |
| author_facet | Narasaka, Koichi Xiao, Yongjun |
| author_sort | Xiao, Yongjun |
| collection | NTU |
| description | During the course of study on the nucleophilic substitution reaction at an sp2
carbon in the Narasaka group, a unique four-membered ring formation was realized by
intramolecular nucleophilic vinylic substitution of a thiolate moiety.
To generalize this 2-alkylidenethietane formation and to get more mechanistic
information, synthesis of 2-alkylidenethietanes were examined by using this newly
developed synthetic methodology.
It was found that 2-alkylidenethietanes were oxidized to 2-alkylidenethietan-
1-oxides by treatment with m-CPBA, which has a unique structure with a strained
four-membered ring, an exo double bond, and a sulfinyl group. Accordingly, the
transformation of 2-alkylidenethietan-1-oxides were investigated. Incidentally, it
was discovered that the treatment of 2-alkylidenethietan-1-oxides with
p-toluenesulfonic acid afforded the unexpected thiophenes. The thiophene formation
was extensively studied in this MSc’s thesis. |
| first_indexed | 2024-10-01T04:05:54Z |
| format | Thesis |
| id | ntu-10356/14732 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:05:54Z |
| publishDate | 2009 |
| record_format | dspace |
| spelling | ntu-10356/147322023-02-28T23:39:13Z Synthesis of 2-Alkylidenethietanes and the transformation to Thiophenes Xiao, Yongjun Narasaka, Koichi School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry During the course of study on the nucleophilic substitution reaction at an sp2 carbon in the Narasaka group, a unique four-membered ring formation was realized by intramolecular nucleophilic vinylic substitution of a thiolate moiety. To generalize this 2-alkylidenethietane formation and to get more mechanistic information, synthesis of 2-alkylidenethietanes were examined by using this newly developed synthetic methodology. It was found that 2-alkylidenethietanes were oxidized to 2-alkylidenethietan- 1-oxides by treatment with m-CPBA, which has a unique structure with a strained four-membered ring, an exo double bond, and a sulfinyl group. Accordingly, the transformation of 2-alkylidenethietan-1-oxides were investigated. Incidentally, it was discovered that the treatment of 2-alkylidenethietan-1-oxides with p-toluenesulfonic acid afforded the unexpected thiophenes. The thiophene formation was extensively studied in this MSc’s thesis. Master of Science 2009-01-21T06:59:23Z 2009-01-21T06:59:23Z 2008 2008 Thesis http://hdl.handle.net/10356/14732 en 80 p. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry Xiao, Yongjun Synthesis of 2-Alkylidenethietanes and the transformation to Thiophenes |
| title | Synthesis of 2-Alkylidenethietanes and the transformation to Thiophenes |
| title_full | Synthesis of 2-Alkylidenethietanes and the transformation to Thiophenes |
| title_fullStr | Synthesis of 2-Alkylidenethietanes and the transformation to Thiophenes |
| title_full_unstemmed | Synthesis of 2-Alkylidenethietanes and the transformation to Thiophenes |
| title_short | Synthesis of 2-Alkylidenethietanes and the transformation to Thiophenes |
| title_sort | synthesis of 2 alkylidenethietanes and the transformation to thiophenes |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | http://hdl.handle.net/10356/14732 |
| work_keys_str_mv | AT xiaoyongjun synthesisof2alkylidenethietanesandthetransformationtothiophenes |