A mechanistic study of a novel chemiluminescent reaction of arylhalides with LiTMP
| Project/Area Number |
17550043
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Yokohama City University |
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Principal Investigator |
TUKADA Hideyuki Yokohama City University, Internaticnal Graduate School of Artsand Sciences, Associate Professor, 大学院国際総合科学研究科, 准教授 (40171970)
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| Project Period (FY) |
2005 – 2006
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| Project Status |
Completed (Fiscal Year 2006)
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| Budget Amount *help |
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2006: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2005: ¥2,800,000 (Direct Cost: ¥2,800,000)
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| Keywords | chemiluminescence / luminescence / lithium reagent / organic chemistry / mechanism |
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| Research Abstract |
We found a new chemiluminescent reaction, an arylhalide with lithium 2,2,6,6-tetramethylpiperidide (LiTMP) in tetrahydrofuran (THF). Owing to increasing importance of the luminescent process, mechanism of our chemiluminescent reaction was investigated.
The luminescence spectrum had an emission maximum at 610 nm. The spectrum was measured by use of optical fibers and a CCD detector. After aqueous work-up and subsequent column chromatograpy, we obtained a TMP substituted product and tetramethoxyanthracene. Fluorescent spectra of these products showed that these species did not correspond to that showing an emission maximum at 610nm. The chemiluminescence is not observed when the solvent was replaced with n-hexane, diphenyl ether, and diethyl ether. The reaction in THF proceeds via benzyne and benzyne-adduct with the enolate derived from THF, and finally gives anthracene derivative. Thus these potentially high-energy molecules are candidates for luminescent molecules.
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Report
(3 results)
Research Products
(9 results)
