Layered Compounds. XXXVI. Structure and Properties of Triple-layered Metaparacyclophanes

The geometrical structures of triple-layered metaparacyclophanes are discussed on the basis of the chemical shifts of the NMR spectra and their temperature dependence. [2.2]Metacyclo(4,7)[2.2]paracyclophane 1 and [2.2]metacyclo(12,15)[2.2]metaparacyclophane 2 proved to be mixtures of conformational...

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Published inBulletin of the Chemical Society of Japan Vol. 49; no. 11; pp. 3203 - 3207
Main Authors Kannen, Naoki, Otsubo, Tetsuo, Sakata, Yoshiteru, Misumi, Soichi
Format Journal Article
LanguageEnglish
Published The Chemical Society of Japan 01.11.1976
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Abstract The geometrical structures of triple-layered metaparacyclophanes are discussed on the basis of the chemical shifts of the NMR spectra and their temperature dependence. [2.2]Metacyclo(4,7)[2.2]paracyclophane 1 and [2.2]metacyclo(12,15)[2.2]metaparacyclophane 2 proved to be mixtures of conformational isomers due to arrangement of meta-substituted ring. [2.2]Paracyclo(4,6)[2.2]metaparacyclophane 3 was confirmed to be a staircase-shape (anti-form), in contrast to a platform-shape (syn-form) of [2.2]metacyclo(4,6)[2.2]metaparacyclophane 5. In their electronic spectra, 1 and 2 exhibit a transannular electronic interaction between the benzene rings similar to that of multilayered [2.2]paracyclophanes; 3 and 5 show one similar to that of multilayered [2.2]metacyclo-phanes. The difference between the former and the latter groups seems to arise from the substitution modes of methylene bridges attached to the inside benzene of triple-layered metaparacyclophanes.
AbstractList Abstract The geometrical structures of triple-layered metaparacyclophanes are discussed on the basis of the chemical shifts of the NMR spectra and their temperature dependence. [2.2]Metacyclo(4,7)[2.2]paracyclophane 1 and [2.2]metacyclo(12,15)[2.2]metaparacyclophane 2 proved to be mixtures of conformational isomers due to arrangement of meta-substituted ring. [2.2]Paracyclo(4,6)[2.2]metaparacyclophane 3 was confirmed to be a staircase-shape (anti-form), in contrast to a platform-shape (syn-form) of [2.2]metacyclo(4,6)[2.2]metaparacyclophane 5. In their electronic spectra, 1 and 2 exhibit a transannular electronic interaction between the benzene rings similar to that of multilayered [2.2]paracyclophanes; 3 and 5 show one similar to that of multilayered [2.2]metacyclo-phanes. The difference between the former and the latter groups seems to arise from the substitution modes of methylene bridges attached to the inside benzene of triple-layered metaparacyclophanes.
The geometrical structures of triple-layered metaparacyclophanes are discussed on the basis of the chemical shifts of the NMR spectra and their temperature dependence. [2.2]Metacyclo(4,7)[2.2]paracyclophane 1 and [2.2]metacyclo(12,15)[2.2]metaparacyclophane 2 proved to be mixtures of conformational isomers due to arrangement of meta-substituted ring. [2.2]Paracyclo(4,6)[2.2]metaparacyclophane 3 was confirmed to be a staircase-shape (anti-form), in contrast to a platform-shape (syn-form) of [2.2]metacyclo(4,6)[2.2]metaparacyclophane 5. In their electronic spectra, 1 and 2 exhibit a transannular electronic interaction between the benzene rings similar to that of multilayered [2.2]paracyclophanes; 3 and 5 show one similar to that of multilayered [2.2]metacyclo-phanes. The difference between the former and the latter groups seems to arise from the substitution modes of methylene bridges attached to the inside benzene of triple-layered metaparacyclophanes.
Author Misumi, Soichi
Kannen, Naoki
Sakata, Yoshiteru
Otsubo, Tetsuo
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Snippet The geometrical structures of triple-layered metaparacyclophanes are discussed on the basis of the chemical shifts of the NMR spectra and their temperature...
Abstract The geometrical structures of triple-layered metaparacyclophanes are discussed on the basis of the chemical shifts of the NMR spectra and their...
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