As a result of our ongoing studies on resorcarenes, we obtained three new resorc[5]arene decamethyl ethers 3a–3c containing cyanomethyl side chains together with the three previously described resorc[4]arenes 2a–2c by treatment of 2-(2,4-dimethoxyphenyl)acrylonitrile (1) with BF3·Et2O. From the X-ray crystallographic structure of 3a, molecular mechanics calculations of the three novel stereoisomers in the gas phase, and the NMR spectroscopic data, the three compounds were attributed architectures of partial 1,3-alternate (3a), partial cone (3b) and partial 1,2-alternate (3c). The relative positions of the substituents were determined by DIF NOE experiments.

Cyanoresorc[5]arenes: Isolation, conformation and crystal structure / D'Acquarica, Ilaria; Laura, Nevola; Giuliano Delle, Monache; Eszter Gacs, Baitz; Chiara, Massera; Franco, Ugozzoli; Giovanni, Zappia; Botta, Bruno. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2006:16(2006), pp. 3652-3660. [10.1002/ejoc.200600169]

Cyanoresorc[5]arenes: Isolation, conformation and crystal structure

D'ACQUARICA, Ilaria;BOTTA, Bruno
2006

Abstract

As a result of our ongoing studies on resorcarenes, we obtained three new resorc[5]arene decamethyl ethers 3a–3c containing cyanomethyl side chains together with the three previously described resorc[4]arenes 2a–2c by treatment of 2-(2,4-dimethoxyphenyl)acrylonitrile (1) with BF3·Et2O. From the X-ray crystallographic structure of 3a, molecular mechanics calculations of the three novel stereoisomers in the gas phase, and the NMR spectroscopic data, the three compounds were attributed architectures of partial 1,3-alternate (3a), partial cone (3b) and partial 1,2-alternate (3c). The relative positions of the substituents were determined by DIF NOE experiments.
2006
macrocyclic compounds; resorc[5]arenes
01 Pubblicazione su rivista::01a Articolo in rivista
Cyanoresorc[5]arenes: Isolation, conformation and crystal structure / D'Acquarica, Ilaria; Laura, Nevola; Giuliano Delle, Monache; Eszter Gacs, Baitz; Chiara, Massera; Franco, Ugozzoli; Giovanni, Zappia; Botta, Bruno. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2006:16(2006), pp. 3652-3660. [10.1002/ejoc.200600169]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/364970
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