Synthesis and Crystal Structure Determination of 4’,9’,4”,9”-Tetra- t -Butyl- 1’,6’,1”,6”-Tetramethoxy-2,5-Dithia[3.3] Metabiphenylophane

作者: Tetsuji Moriguchi , Tatsuya Egami , Daisuke Yakeya , Venkataprasad Jalli , Kenji Yoza

DOI: 10.4236/CSTA.2016.53005

关键词: Condensation reactionBiphenylCrystal structureSingle crystalCrystallographyConformational isomerismCalixareneChemistryCrystalDihedral angle

摘要: The title compound 4’,9’,4”,9”-tetra-tert-butyl-1’,6’,1”,6”-tetramethoxy-2,5-dithia[3.3] metabiphenylophane was synthesized as a calixarene like large-sized metacyclophane from the corresponding 3,3’-bis(chloromethyl)-5,5’-bis(1,1-dimethylethyl)-2,2’-dimethoxy-1,1’-biphenyl and 3,3’-bis (mercaptomethyl)-5,5’-bis(1,1-dimethylethyl)-2,2’-dimethoxy-1,1’-biphenyl via an intermolecular condensation reaction. characterized using 1H NMR spectroscopy mass spectrometry. Its exact conformational structure determined single crystal X-ray diffraction analysis. has quite strained 1,2-alternate because of its two high dihedral angled rigid biphenyl parts in crystal. includes isomers different conformers, ratio is 78:22.

参考文章(9)
Virgil Boekelheide, Syntheses and properties of the [2n]Cyclophanes Springer, Berlin, Heidelberg. pp. 87- 143 ,(1983) , 10.1007/3-540-12397-0_2
Louis Korbla Doamekpor, Raphael Kwaku Klake, Vincent Kodzo Nartey, Takehiko Yamato, Oti Gyamfi, Dennis Adotey, Synthesis and Conformational Studies on [3.3.3]Metacyclophane Oligoketone Derivatives, and Their Metal Ion Recognition International Journal of Organic Chemistry. ,vol. 05, pp. 126- 135 ,(2015) , 10.4236/IJOC.2015.52014
Akihiko Tsuge, Nobuko Takagi, Takehiro Kakara, Tetsuji Moriguchi, Kazunori Sakata, Preparation, Conformation and Reaction of Medium-sized [1.n.n]Metacyclophanes Chemistry Letters. ,vol. 29, pp. 948- 949 ,(2000) , 10.1246/CL.2000.948
Graham J. Bodwell, THE NEW INDUCTEES IN THE HALL OF PHANE : NO PHANE, NO GAIN Angewandte Chemie. ,vol. 35, pp. 2085- 2088 ,(1996) , 10.1002/ANIE.199620851
Samah Simaan, Silvio E. Biali, A "classical" tetrahydroxycalix[4]arene adopting the 1,2-alternate conformation. Journal of Organic Chemistry. ,vol. 69, pp. 95- 98 ,(2004) , 10.1021/JO035573J
Yoshimasa. Fukazawa, Yoshiya. Takeda, Shuji. Usui, Mitsuaki. Kodama, Synthesis and conformation of 1,1,10,10-tetramethyl[3.3]metacyclophane Journal of the American Chemical Society. ,vol. 110, pp. 7842- 7847 ,(1988) , 10.1021/JA00231A039
Tetsuji Moriguchi, Tatsuya Egami, Akihiko Tsuge, Synthesis and Molecular Structure of 4′,9′,4″,9″-Tetra-tert-butyl-1′,6′,1″,6″-tetramethoxy-2,5-dioxa[3.3]metabiphenylophane Journal of Crystallography. ,vol. 2014, pp. 1- 7 ,(2014) , 10.1155/2014/695701
George M. Sheldrick, A short history of SHELX Acta Crystallographica Section A. ,vol. 64, pp. 112- 122 ,(2008) , 10.1107/S0108767307043930