Molecular and crystal structure of selected compounds containing 8,11-dioxa[4.3.3]propellane moiety

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• 作者：Pawe&#322 ; Szlachcic^a ; ^{pszlachcic@ar.krakow.pl} ; Przemys&#322 ; aw Kolek^b ; Tomasz Uchacz^c ; Katarzyna Stadnicka^c
• 关键词：Propellanes ; Crystal structures ; DFT calculations ; NMR spectroscopy
• 刊名：Journal of Molecular Structure
• 出版年：2012
• 期刊代码：62_00222860
• 类别：ch
• 出版时间：28 March, 2012
• 卷：1012
• 期：Complete
• 页码：87-96
• 文件大小：1278 K

摘要

The molecular and crystal structures of two derivatives containing 8,11-dioxa[4.3.3]propellane moiety: 8,11-dioxa[3,4-(4鈥?methylbenzo)]-[4.3.3]propellane and 8,11-dioxa[3,4-(4鈥?tert-butylbenzo)]-[4.3.3]propellane, were determined and compared with those found for 1,2,4,5-bis{8鈥?11鈥?dioxa[4.3.3]propella(3鈥?4鈥?}benzene. The discussion of the most stable conformation of cyclohexene and tetrahydrofurane rings for isolated 8,11-dioxa(3,4-benzo)]-[4.3.3]propellane molecule was made using the DFT calculations. The results were compared with those performed for tetraline and 2,2,3,3-tetramethyltetraline. 8,11-Dioxa[3,4-(4鈥?methylbenzo)]-[4.3.3]propellane is important as a reference compound because the unsubstituted 8,11-dioxa(3,4-benzo)-[4.3.3]propellane cannot be obtained in the form of crystalline phase suitable for X-ray diffraction. ¹H NMR spectroscopic analysis showed that the methyl group does not induce expected splitting of the appropriate signals, observed in the case of tert-butyl derivative.