1999 Fiscal Year Final Research Report Summary
Syntheses of Novel Belt-Type Molecules Using Dewar Benzenes.
| Project/Area Number |
09640620
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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 | HOKKAIDO UNIVERSITY |
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Principal Investigator |
OHKITA Masakazu Hokkaido University, Grad. School of Science, Instructor, 大学院・理学研究科, 助手 (60211786)
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| Co-Investigator(Kenkyū-buntansha) |
TSUJI Takashi Hokkaido University, Grad. School of Science, Professor, 大学院・理学研究科, 教授 (20029482)
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| Project Period (FY) |
1997 – 1999
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| Keywords | Dewar Benzenes / Belt-Type Molecules / Cyclophanes / Paraphenylene / Bisdiene |
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| Research Abstract |
We have successfully synthesized and characterized novel p-phenylene-based strained macrocycles by introducing 1,4-acetal-bridged Dewar benzene as a building block. The present results demonstrate that a Dewar benzene unit can be exploited as a masked p-phenylene unit for the constraction of strained macrocyclic systems. By using other spacers and/or connection modes, a variety of p-phenylene-containing strained macrocycles with unique structures and properties may well become available based on the present building block aproach.
We have also successfully developed a new bisdiene molecule that produces a Dewar benzene skeleton upon two successive Diels-Alder reactions with activated dienophiles. Dehydrogenation of the 1: 2 adducts provides the corresponding Dewar form of polyacenes. Similar bisdiene systems possessing other 1,4-bridging units may also be available based on the synthetic scheme. Therefore, the present results open a unique and versatile route to Dewar derivatives which, in turn, would be regarded as potential precursors for novel cyclophanes as well as belt-type molecules.
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