Synthesis of Cyclophanes with Intra-Annular Functionality and Cage Structure
| Autor: | Perumal Rajakumar, Arunachalam Kannan, V. Kabaleeswaran, S. S. Rajan |
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| Rok vydání: | 1996 |
| Předmět: | |
| Zdroj: | The Journal of Organic Chemistry. 61:5090-5102 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo950957y |
| Popis: | Cyclophanes of the type 1 and 2, with large cavity sizes, have been synthesized from the corresponding dichloride 8 or 8a and o-xylene-�,�?-dithiol (9), p-xylene-�,�?-dithiol (10), or m-terphenyldithiol (11). Similarly, cyclophanes of the type 3 with intra-annular functionality have been obtained by the coupling of the corresponding dithiol 15 or 19 and m-terphenyl dibromide 5, 5a, 5b, or 5c. With the aim of introducing multifunctionality, cyclophanes of the type 21 and 23 were prepared from 3,5-bis(mercaptomethyl)anisole or 3,5-bis(mercaptomethyl)phenol and the corresponding substituted m-terphenyl dibromide 5b or 5c. Cyclophanes 24, 24a, 24b, and 32, with a new type of cage structure, have been obtained by the coupling of the corresponding tetrathiol 29 with 2 equiv of the dibromides 5c, 5a, and 5b or 1 equiv of the tetrabromide 31, respectively. Further, the sodium salts of the cyclophanes 3c, 21, and 24b were completely characterized by 1H NMR spectroscopy. XRD analysis of the cyclophane 21 revealed the presence of an ethanol molecule inside the cavity, indicating the facile formation of a host-guest complex. |
| Databáze: | OpenAIRE |
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