New mechanism for the reaction of thianthrene cation radical perchlorate with tert-butyl peroxide

Bulletin of the Korean Chemical Society

Volumn 23, Issue 1, 2002, Pages 103-106

  Park, Bo Kyung ^a   Sohn, Chang Kook ^a   Lee, Wang Keun ^a  

^a Chonnam National University   (South Korea)

Author keywords

B3LYP and CBS 4 methods; T Butyl peroxide; Thianthrene cation radical

Indexed keywords

ACETAMIDE DERIVATIVE; ACETONITRILE; CATION; MACROCYCLIC COMPOUND; N TERT BUTYL ACETAMIDE; PERCHLORATE; PEROXIDE; RADICAL; TERT BUTYL PEROXIDE; THIANTHRENE; THIANTHRENE 5 OXIDE; THIANTHRENE 5,5 DIOXIDE; THIANTHRENE CATION RADICAL; UNCLASSIFIED DRUG;

ARTICLE; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS;

EID: 0037138248     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2002.23.1.103     Document Type: Article

References (25)

1. Matsugo, S.; Saito, I. In Organic peroxides; Ando, W., Ed.; Wiley: New York, 1992; pp 157-194.
2. Huyser, E. S. In Free-Radical Chain Reactions; Wiley-interscience: New York, 1970; p 287.
3. Shin, J.; Kim, K. Bull. Korean Chem. Soc. 1984, 5, 211.
4. 2; 248 (100), 216 (12), 200 (38), 184 (20), 171 (18), 139 (13), 108 (11), 100 (10).
5. Bae, D. H.; Engel, P. S.; Hoque, A. K. M. M.; Keys, D. E.; Lee, W. K.; Shaw, R. W.; Shine, H. J. J. Am. Chem. Soc. 1985, 107, 2561.
6. Lee, W. K.; Chung, C. T. Bull. Korean Chem. Soc. 1992, 13, 694.
7. Chung, J. H.; Lim, S.-H.; Sohn, C. K.; Lee, W. K. Bull. Korean Chem. Soc. 1998, 19, 792.
8. Park, Y. S.; Lee, W. K. Bull. Korean Chem. Soc. 1997, 18, 360.
9. Choi, J. M.; Ma, E.-K.; Sohn, C. K.; Lee, W. K. Bull. Korean Chem. Soc. 2000, 21, 1254.
10. Park, Y. S.; Han, D. S.; Lee, W. K. Bull. Korean Chem. Soc. 1998, 19, 615.
11. Shine, H. J.; Murata, Y. J. Org. Chem. 1969, 34, 3368.
12. Chiou, S.; Hoque, A. K. M. M.; Shine, H. J. J. Org. Chem. 1990, 55, 327.
13. Shine, H. J.; Yueh, W. J. Org. Chem. 1994, 59, 3553.
14. Han, D. S.; Shine, H. J. J. Org, Chem. 1996, 61, 3997.
15. (a) Montgomery, J. A., Jr.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1994, 101, 5900.
16. (b) Ochterski, J. W.; Petersson, G. A.; Montgomery, J. A. J. Chem. Phys. 1996, 104, 2598.
17. (a) Becke, A. D. J. Chem. Phys. A 1993, 98, 5648.
18. (b) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
19. (c) Parr, R. G.; Yang, W. In Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
20. For example, geometry optimization and then frequency calculations for the cation radical took 14 h, respectively, on a compaq GS320 supercom. In comparision, corresponding B3LYP/6-311G computations took a total of 33.5 h.
21. (a) Wilson, E. B.; Cross, P. C. In Molecular Vibrations; McGraw-Hill: New York, 1955.
22. (b) Hehre, W. J.; Radom, L.; Schleyer, P. V. R.; Pople, J. A. In Ab initio Molecular Orbital Theory; Wiley: New York, 1986.
23. Adam, W.; Hass, W.; Sieker, G. J. Am. Chem. Soc. 1984, 106, 5020.
24. Adam, W.; Golsch, D. J. Org. Chem. 1997, 62, 115.
25. Ritter, J. J.; Minieri, P. P. J. Am. Chem. Soc. 1948, 70, 4045.