Synthesis of Anthryl Sulfides from Anthryl Methyl Ethers via Acid-Catalyzed Ether-Sulfide Exchange Reaction

Abstract

Under acidic condition, anthryl methyl ethers behave as anthryl cation synthons and undergo ipso-substitution to produce anthryl sulfides. These compounds are hard to access with currently available methodology and they have great potentials as organic electronic materials.

Key words

arene - nucleophilic aromatic substitution - hetero­cycles - ­macrocycles - sulfur

References

• 1a Kivelson S. Chapman OL. Phys. Rev. B  1983,  28:  7236 
• 1b Kertesz M. Hoffmann R. Solid State Commun.  1983,  47:  97 
• 1c Houk KN. Lee PS. Nendel M. J. Org. Chem.  2001,  66:  5517 
• 1d Bendikov M. Duong HM. Starkey K. Houk KN. Carter EA. Wudl F. J. Am. Chem. Soc.  2004,  126:  7416 
• 2a Lin Y.-Y. Gundlach DJ. Nelson S. Jackson TN. IEEE Trans. Electron Devices  1997,  44:  1325 
• 2b Dimitrakopoulos CD. Malenfant PRL. Adv. Mater.  2002,  14:  99 
• 3a Pope M. Kallmann HP. Magnante P. J. Chem. Phys.  1963,  38:  2042 
• 3b Zheng S. Shi J. Chem. Mater.  2001,  13:  4405 
• 3c Danel K. Huang T.-H. Lin JT. Tao Y.-T. Chuen C.-H. Chem. Mater.  2002,  14:  3860 
• 4 Ito K. Suzuki T. Sakamoto Y. Kubota D. Inoue Y. Sato F. Tokito S. Angew. Chem. Int. Ed.  2003,  42:  1159 
• 5a Doering WVE. Sarma K. J. Am. Chem. Soc.  1992,  114:  6037 
• 5b Heiko I. Eur. J. Org. Chem.  1999,  1595 
• 6a Antolini L. Borsari M. Goldoni F. Iarossi D. Mucci A. Schenetti L. J. Chem. Soc., Perkin Trans. 1  1999,  3207 
• 6b Tucker JHR. Gingras M. Brand H. Lehn J.-M. J. Chem. Soc., Perkin Trans. 2  1997,  1303 
• 6c Lee WK. Heiney PA. McCauley JP. Smith AB. Mol. Cryst. Liq. Cryst.  1991,  198:  273 
• 6d Mizuno M. Garito AF. Cava MP. J. Chem. Soc., Chem. Commun.  1978,  18 
• 7a Kwong FY. Buchwald SL. Org. Lett.  2002,  4:  3517 
• 7b Bates CG. Gujadhur RK. Venkataraman D. Org. Lett.  2002,  4:  2802 
• 8 Lin C.-H. Radhakrishnan K. Chem. Commun.  2005,  504 
• Sporadic examples of similar exchange reaction of two particular compounds (one naphthalene and one thiophene derivative) appeared in the literature during the course of our study. To the best of our knowledge, the present study is the first systematic exploration of such exchange reaction on any type of substrate. See:
• 9a Areephong J. Ruangsupapichart N. Thongpanchang T. Tetrahedron Lett.  2004,  45:  3067 
• 9b Hellberg J. Remonen T. Allared F. Slaett J. Svensson M. Synthesis  2003,  2199 
• 10a Eliel EL. Stereochemistry of Carbon Compounds   McGraw-Hill Book; New York: 1962.  p.265 
• 10b Illuminati G. Mandolini L. Acc. Chem. Res.  1981,  14:  95