Cycloaddition of Bis(3,3-bis(diethylamino)thioacryloyl) Disulfide with Alkynic Dienophiles: A New Access to 2H-Thiopyran-2-thiones.
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- Akimoto Keiichi
- Department of Chemistry, Faculty of Science, Saitama University
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- Masaki Kazuto
- Department of Chemistry, Faculty of Science, Saitama University
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- Nakayama Juzo
- Department of Chemistry, Faculty of Science, Saitama University
Bibliographic Information
- Other Title
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- Cycloaddition of Bis〔3,3-bis(diethylamino)thioacryloyl〕Disulfide with Alkynic Dienophiles:A New Access to 2H-Thiopyran-2-thiones
- Cycloaddition of Bis 3 3-bis diethylami
- Cycloaddition of Bis[3,3-bis(diethylamino)thioacryloyl] Disulfide with Alkynic Dienophiles: A New Access to 2<i>H</i>-Thiopyran-2-thiones
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Abstract
The reaction of bis[3,3-bis(diethylamino)thioacryloyl] disulfide (1) with dimethyl acetylenedicarboxylate gave dimethyl 4-diethylamino-2-thioxo-2H-thiopyran-5,6-dicarboxylate in 69% yield. Similarly, a series of alkynic dienophiles reacted with 1 to give the corresponding 2H-thiopyran-2-thione derivatives in modest-to-reasonable yields. A full experimental description of this 2H-thiopyran-2-thione formation is given and a mechanism involving [4+2]cycloaddition followed by homolytic cleavage of the S–S bond is presented.
Journal
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 69 (7), 2091-2094, 1996
The Chemical Society of Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390001204122024448
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- NII Article ID
- 10008906481
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- NII Book ID
- AA00580132
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- ISSN
- 13480634
- 00092673
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- NDL BIB ID
- 4060476
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed