1995 Fiscal Year Final Research Report Summary
Study on the Novel Radical Reactions with Hypervalent Iodine Compounds
| Project/Area Number |
06640762
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
物質変換
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| Research Institution | Chiba University |
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Principal Investigator |
TOGO Hideo Chiba University, Department of Chemistry Faculty of Science, Associate Professor, 理学部, 助教授 (60217461)
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| Project Period (FY) |
1994 – 1995
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| Keywords | Radical reaction / Carbon-centered radical / Oxygen-centered radical / Nitrogen-centered radical / (Diacyloxyiodo) arene / Radical cyclization |
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| Research Abstract |
Radical reactions are one of the most useful methods for organic synthesis. Therefore, the study on the novel radical reactions with trivalent iodine compounds has been carried out. As a result, it was found that (diacyloxyiodo) arenes which has electron-donating group on a aromatic ring accelerated the radical reactivities under the irradiation with tungsten lamp as shown below,
1) conversion of carboxylic acids to the corresponding sulfides in the presence of disulfides,
2) conversion of aromatic carboxylic acids to the corresponding gamma-or delta-lactones,
3) conversion of alcohols bearing a aromatic ring to the corresponding cyclic ethers,
4) conversion of amines bearing a aromatic ring to the corresponding cyclic amines,
These reactions proceed via the formation of carbon-, oxygen-, and nitrogen-centered radicals to give the products with a simple operation in good yields. In nature, there are many kinds of important cyclic compounds containing oxygen and nitrogen atoms. Therefore, the present method is very useful for the preparation of these natural products. These results were published in three international Journals in 1995, and the other papers are in preparation for the contribution to the Journals.
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