| Project/Area Number |
12640512
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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 | Saitama University |
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Principal Investigator |
HASEGAWA Toshio Saitama Unniversity, Faculty of Science, Assistant Professor, 理学部, 助教授 (00237976)
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| Co-Investigator(Kenkyū-buntansha) |
MACHIGUCHI Takahisa Saitama Unniversity, Faculty of Science, Professor, 理学部, 教授 (00008864)
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| Project Period (FY) |
2000 – 2002
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| Project Status |
Completed (Fiscal Year 2002)
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| Budget Amount *help |
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 2002: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2001: ¥1,200,000 (Direct Cost: ¥1,200,000)
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| Keywords | monothiotropolone / equilibrium / azulene / troponolid / activated methylene compound / カルボニル / π電子 / NMR / IR / 分子軌道法 / 共役 / トロポン / ベンザイン / Diels-Alder |
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| Research Abstract |
We have found the following results,
1. Novel solid-state propertie :
Tropolone exsits as an last equilibrium mixture of a ketone form and an enol form. This equilibrium of tropolone is extremely fast in solution, but is frozened on the NMR time scale in the solid state. Monthiotropolone is the sulfur analogue of tropolone. We have found that this compound exists as extremely fast equilibrium mixture both in solution and in the solid state. This novel behavior in the solid-state is found to be due to packing arrangement of monothiotropolone.
2. Azulene synthesis in the reaction of an activated trponoid compound with an activated methylene compound :
Reaction of activated troponoid compounds with activated methylene compounds gave azulenes in good yields. These reactions are useful methods to obtain azulene derivatives with polyfunctional groups in five-membered ring moiety. We investigated the reaction mechanism of 2-methoxytropone with malonouilrilc to give an azulene and found the detailed reaction path of many steps containing several equilibrium processes.
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