Methylene: The Linker of Two Aromatic Iminium Salts

  • Anurag Noonikara-Poyil University of Texas at Arlington
  • Enrique Barragan University of Texas at Arlington
  • Siddappa Patil Jain University
  • Alejandro Bugarin University of Texas at Arlington
Keywords: Aromatic iminium salts, Pi-conjugated triazene, X-ray structure, iodomethane, methylene chloride.

Abstract

A straightforward synthesis of aromatic iminium salts has been developed by coupling 2-Azido-1,3,5-trimethyl benzene with 1,3-ditert-butylimidazolium tetrafluoroborate in basic conditions, followed by treatment with dichloromethane or iodomethane. Herein, we report the synthetic procedure and full characterization data, including X-ray structure analysis, of the expected bis(triazenyl)methane adduct 5. Moreover, we have discovered what constitutes a double carbon-chlorine bond activation.

Author Biography

Alejandro Bugarin, University of Texas at Arlington

Assistant Professor

Department of Chemistry and Biochemistry

References

Howell, J. M.; Feng, K.; Clark, J. R.; Trzepkowski, L. J.; White, M. C. J. Am. Chem. Soc. 2015, 137, 14590-14593.

Andrez, J.-C. Beilstein J. Org. Chem. 2009, 5, 33.

Baumann, M.; Baxendale, I. R.; Ley, S. V.; Nikbin, N. Beilstein J. Org. Chem. 2011, 7, 442-495.

Assary, R. S.; Brushett, F. R.; Curtiss, L. A. RSC Adv. 2014, 4, 57442-57451.

Chiba, S. Synlett 2012, 2012, 21-44.

Patil, S.; White, K.; Bugarin, A. Tetrahedron Lett. 2014, 55, 4826–4829.

Patil, S.; Bugarin, A. Acta Crystallogr., Sect. E: Struct. Rep. Online 2014, 70, 224–227

Patil, S.; Bugarin, A. Eur. J. Org. Chem. 2016, 2016, 860−870.

Pogoreltsev, A.; Tulchinsky, Y.; Fridman, N.; Gandelman, M. J. Am. Chem. Soc. 2017, 139, 4062-4067.

Back, J.; Park, J.; Kim, Y.; Kang, H.; Kim, Y.; Park, M. J.; Kim, K.; Lee, E. J. Am. Chem. Soc. 2017, 139, 15300-15303.

Barragan, E.; Bugarin, A. J. Org. Chem. 2017, 82, 1499–1506.

Barragan, E.; Noonikara-Poyil, A.; Yang, C-H.; Wang, H.; Bugarin, A. Org. Chem. Front. 2019, 6, 152–161.

Zincsuk, J.; Carnavale, G. A. Arkivoc 2016, 4, 352–362.

Pattacini, R.; Jie, S.; Braunstein, P. Chem. Commun. 2009, 890-892.

Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1958, 80, 5323-5324.

Rossberg, M. , Lendle, W. , Pfleiderer, G. , Tögel, A. , Dreher, E. , Langer, E. , Rassaerts, H. , Kleinschmidt, P. , Strack, H. , Cook, R. , Beck, U. , Lipper, K. , Torkelson, T. R., Löser, E. , Beutel, K. K. and Mann, T. (2006). Chlorinated Hydrocarbons. In Ullmann's Encyclopedia of Industrial Chemistry, (Ed.).

Archer, R. H.; Zones, S. I.; Davis, M. E. Microporous Mesoporous Mater. 2010, 130, 255-265.

Lu, Y.; Wang, L.; Wang, X.; Xi, T.; Liao, J.; Wang, Z.; Jiang, F. Eur. J. Med. Chem., 2017, 135, 125-141.

For additional crystallography data of compound 5 in CIF and other formats, see the CCDC 1832942.

Published
10-17-2019