Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes

Synthesis

Volumn , Issue 1, 2008, Pages 110-114

  Barton, Olaf G ^a   Mattay, Jochen ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

Calixarenes; Iodination; Oxidative halogenation; Peroxides; Phase transfer catalysis

Indexed keywords

CALIXARENES; IODINATION; OXIDATIVE HALOGENATION; PHASE TRANSFER CATALYSIS;

ACETONITRILE; CATALYST ACTIVITY; HALOGENATION; IODINE COMPOUNDS; OXIDANTS; PEROXIDES; SOLUBILITY; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

5,11,17,23 TETRAIODOCALIX[4]ARENE 25,26,27,28 TETRA N DODECYLETHER; 5,11,17,23 TETRAIODOCALIX[4]ARENE 25,26,27,28 TETRA N PROPYLETHER; ACETONITRILE; AROMATIC COMPOUND; BICARBONATE; CALIX[4]ARENE DERIVATIVE; CALIXARENE; CHLOROFORM; IODINE; METHYLTRIPHENYLPHOSPHONIUM PEROXODISULFATE; SODIUM PEROXODISULFATE; SULFATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; IODINATION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; SOLUBILITY;

EID: 38349143445     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1000826     Document Type: Article

References (27)

1. (a) Timmerman, P.; Verboom, W.; Reinhoudt, D. N.; Arduini, A.; Grandi, S.; Sicuri, A. R.; Pochini, A.; Ungano, R. Synthesis 1994, 185.
2. (b) Gu, T.; Ceroni, P.; Marconi, G.; Armaroli, N.; Nierengarten, J.-F. J. Org. Chem. 2001, 66, 6432.
3. (c) Arduini, A.; Giorni, G.; Pochini, A.; Secchi, A.; Ugozzoli, F. J. Org. Chem. 2001, 66, 8302.
4. (d) Matthews, S. E.; Felix, V.; Drew, M. G. B.; Beer, P. D. Org. Biomol. Chem. 2003, 1, 1232.
5. (e) Barton, O. G.; Schmidtmann, M.; Müller, A.; Mattay, J. New. J. Chem. 2004, 28, 1335.
6. (f) Wong, M. S.; Xia, P. F.; Lo, P. K.; Sun, X. H.; Wong, W. Y.; Shuang, S. J. Org. Chem. 2006, 71, 940.
7. (a) Zhang, Y.; Shibatomi, K.; Yamamoto, H. Synlett 2005, 2837.
8. (b) Yadav, J. S.; Reddy, B. V. S.; Reddy, P. S. R.; Basak, A. K.; Narsaiah, A. V. Adv. Synth. Catal. 2004, 346, 77.
9. (c) Johnsson, R.; Meijer, A.; Ellervik, U. Tetrahedron 2005, 61, 11657.
10. (d) Branytska, O. V.; Neumann, R. J. Org. Chem. 2003, 68, 9510.
11. (e) Jafarzadeh, M.; Amani, K.; Nikpour, F. Can. J. Chem. 2005, 83, 1808.
12. (f) Wan, S.; Wang, S. R.; Lu, W. J. Org. Chem. 2006, 71, 4349.
13. (g) Tilve, R. D.; Alexander, V. M.; Khadilkar, B. M. Tetrahedron Lett. 2002, 43, 9457.
14. (h) Sosnowski, M.; Skulski, L. Molecules 2005, 10, 401.
15. (a) Firouzabadi, H.; Iranpoor, N.; Garzan, A. Adv. Synth. Catal. 2005, 347, 1925.
16. (b) Mohan, K. V. V. K.; Narender, N.; Kulkarni, S. J. Tetrahedron Lett. 2004, 45, 8015.
17. (c) Narender, N.; Srinivasu, P.; Kulkarni, S. J.; Raghavan, K. V. Synth. Commun. 2002, 32, 2319.
18. (d) Hajipour, A. R.; Adibi, H. J. Chem. Res., Synop. 2004, 294.
19. (e) Iskra, J.; Stavber, S.; Zupan, M. Synthesis 2004, 1869.
20. (f) Pourali, A. R.; Ghanei, M. Chin. J. Chem. 2006, 24, 1077.
21. (g) Zielinska, A.; Skulski, L. Molecules 2005, 10, 1307.
22. (h) Yang, S. G.; Kim, Y. H. Tetrahedron Lett. 1999, 40, 6051.
23. (i) Park, M. Y.; Yang, S. G.; Kim, Y. H. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 1235.
24. (j) Hajipour, A. R.; Ruoho, A. E. Org. Prep. Proced. Int. 2005, 37, 279.
25. (a) Dondoni, A.; Marra, A.; Scherrmann, M.-C.; Casnati, A.; Sansone, F.; Ungaro, R. Chem. Eur. J. 1997, 3, 1774.
26. (b) Shahgaldian, P.; Coleman, A. W.; Kuduva, S. S.; Zaworotko, M. J. Chem. Commun. 2005, 1968.
27. SDBSWeb site: http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology, 09-25-2007).