2002 Fiscal Year Final Research Report Summary
Novel Kinetic Stabilization of the [1.1] Paracyclophane System and Preparation of the Naphthalenophane System
| Project/Area Number |
13640521
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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 |
KAWAI Hidetoshi Hokkaido Univ., Grad. School of Sci., Assist. Prof., 大学院・理学研究科, 助手 (50322798)
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| Co-Investigator(Kenkyū-buntansha) |
TSUJI Takashi Hokkaido Univ., Grad. School of Sci., Prof., 大学院・理学研究科, 教授 (20029482)
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| Project Period (FY) |
2001 – 2002
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| Keywords | Cyclophane / Strained Compounds / Dewar benzene / Photochromic / Kinetic Stabilization / Extended Conjugation / Aromatic Compounds / Transannular Interaction |
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| Research Abstract |
A kinetic stabilization of the [1.1]paracyclophane system was examined by structurally modifying the methylene bridges. This approach allows introductlon of a variety of substituents on the benzene rlngs of [1.1]paracyclophane. The bis (Dewar benzene) derivative, the precursor of [1.1]paracyclophane, bearing t-BuMe_2SiO groups on the bridges prepared in 21 steps. Photoirradiation to this compound at 77K resulted in the formation of labile [1.1]paracyclophane but accompanied by other byproducts. To investigate the reactivity and stability of this new type of [1.1]paracyclophanes bearing different groups in this position was also prepared.
The [1.1]naphthalenophanes exhibiting extended conjugation of the [1.1]paracyclophane π-system were designed in anticipation of the enhanced transannular effect. In the course of preparation of their precursors, a novel benzo-annulation method consisting of [2+2]photocycloaddition of olefins to benzoquinone bis (ethylene ketal), deprotection of ketals and spontaneous aromatization steps was developed. Synthetic study of [1.1]naphthalenophane derivatives is now under way by this methods.
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Research Products
(9 results)
