Demethylation of an Allene Bearing Two Dimethoxythioxanthene Groups by Oxidation via a Vinyl Cation Intermediate
Australian Journal of Chemistry 63 巻 12 号
1638-1644 頁
2010-12-06 発行
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| ファイル情報(添付) | |
| タイトル ( eng ) |
Demethylation of an Allene Bearing Two Dimethoxythioxanthene Groups by Oxidation via a Vinyl Cation Intermediate
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| 作成者 |
Yamaguchi Torahiko
Fuku-en Shin-ichi
Sugawara Shun
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| 収録物名 |
Australian Journal of Chemistry
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| 巻 | 63 |
| 号 | 12 |
| 開始ページ | 1638 |
| 終了ページ | 1644 |
| 抄録 |
With the objective of preparing an isolable triplet carbene, we have carried out the oxidation of an allenic compound bearing two thioxanthene moieties (5). Relatively weak oxidants such as Ph3C+BF4 – gave 8, which is the conjugate acid of 5, as a result of a one-electron oxidation followed by hydrogen abstraction, whereas relatively strong oxidants such as SbCl5 furnished a dicationic ketal (9) as a consequence of oxidation and demethylation. Computations on the supposed dicationic intermediate suggest that the singlet state is more stable than the triplet state by 6.7 kcal mol–1 and that the reason for this peculiarity is because the singlet state is essentially a vinyl cation stabilized by a coordinating methoxy group.
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| NDC分類 |
化学 [ 430 ]
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| 言語 |
英語
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| 資源タイプ | 学術雑誌論文 |
| 出版者 |
CSIRO Publishing
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| 発行日 | 2010-12-06 |
| 権利情報 |
Copyright (c) 2010 CSIRO
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| 出版タイプ | Author’s Original（十分な品質であるとして、著者から正式な査読に提出される版） |
| アクセス権 | オープンアクセス |
| 収録物識別子 |
[ISSN] 0004-9425
[DOI] 10.1071/CH10297
[NCID] AA00555860
[DOI] http://dx.doi.org/10.1071/CH10297
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