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From four-fold functionalised [3.3]cyclophanes to belt-shaped and multibridged molecules

DOI: 10.1039/P19960002061

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2061 - 2067 (1996)

Update date:2022-07-29

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Authors:

Breidenbach, StefanBreidenbach, Stefan

Harren, JoergHarren, Joerg

Neumann, SusanneNeumann, Susanne

Nieger, MartinNieger, Martin

Rissanen, KariRissanen, Kari

Voegtle, FritzVoegtle, Fritz

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Article abstract of DOI:10.1039/P19960002061

Reaction of the four-fold functionalised cyclophane 7 with tetrafunctionalised aromatic building blocks such as 9 and 10 afforded the new belt-shaped molecules 3 and 4, respectively. The new four-fold bridged cyclophane 8 was synthesised by cyclisation of 7 with tosylamide monosodium salt. The macropolycycle 5, the structure of which has been confirmed by single crystal X-ray analysis, was obtained by cyclisation of the first tetrafunctionalised biphenylophane 15 with the tetrathiol 16. The constitution and conformation of compounds 3, 5 and 8 were examined by VT-NMR studies and HH-NOE experiments. Crystallisation of 8 from two different solvents leads to guest-dependent conformational changes revealed by X-ray analysis. The results described demonstrate that molecular belts and tubes of different type and size are accessible by varying the building blocks within our synthetic strategy.

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Products guided by the article

Product name:6,12,21,27-tetrakis(ethoxycarbonyl)-2,17-bis(4-tolylsulfonyl)-2,17-diaza[3.3](3,3')(3,3')biphenylophane

Cas No:181021-70-5

181021-70-5

R&D Labs maybe for 181021-70-5

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