Layered Compounds. V. Synthesis and Properties of [<I>m</I>.<I>n</I>]Paracyclophadiynes
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概要
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A series of bisethynyl compounds, IX and XII, were prepared by a modified ethynylation using <I>N</I>-methyl-2-pyrrolidone in good yields. Intramolecular oxidative coupling of the bisethynyl compounds has been achieved with high-dilution technique to give relatively good yields of highly strained or strainless [<I>m</I>.<I>n</I>]paracyclophadiynes I and cyclic diacetylenes XIII. From the comparison of the electronic spectra of these diacetylenic compounds, it is concluded that abnormal spectra of Ic and Id are attributed to the transannular π-electronic interaction between benzene nucleus and diacetylenic unit rather than the ring strain in the molecules. In addition, a marked down-field shift of aromatic protons in Ic compared with the other paracyclophadiynes is explained in terms of the transannular shielding effect of diacetylenic linkage.
- 公益社団法人 日本化学会の論文
著者
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Sakata Yoshiteru
The Institute Of Science And Industrial Research Osaka University
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Misumi Soichi
The Institute Of Scientific And Industrial Research Osaka University
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Otsubo Tetsuo
The Institute of Scientific and Industrial Research, Osaka University
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Matsuoka Takahiro
The Institute of Scientific and Industrial Research, Osaka University
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Negi Taichi
The Institute of Scientific and Industrial Research, Osaka University
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