A first example using o-iodoxybenzoic acid (IBX) in combination with tetraethylammonium bromide (TEAB) for ring expansion of 1,3-dithiolanes and 1,3-dithianes

Synlett

Volumn , Issue 9, 2005, Pages 1483-1485

  Shukla, Vidyanand G ^a   Salgaonkar, Paresh D ^a   Akamanchi, Krishnacharya G ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Dithiepines; Dithiins; O iodoxybenzoic acid (IBX); Tetraethylammonium bromide (TEAB)

Indexed keywords

1,3 DITHIANE DERIVATIVE; 1,3 DITHIOLANE DERIVATIVE; 2 IODYLBENZOIC ACID; BENZOIC ACID DERIVATIVE; DIHYDRO 1,4 DITHIEPINE; DIHYDRO 1,4 DITHIIN; TETRYLAMMONIUM BROMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 20544475833     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-868496     Document Type: Article

References (26)

1. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
2. (a) Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. J. Am. Chem. Soc. 2000, 722, 7596.
3. (b) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245.
4. (c) Ref. I and references cited therein.
5. Nicolaou, K. C.; Montagnon, T.; Baran, P. S. Angew. Chem. Int. Ed. 2002, 41, 1386.
6. (a) Ramanarayanan, G. V.; Shukla, V. G.; Akamanchi, K. G. Synlett 2002, 2059.
7. (b) Chaudhari, S. S.; Akamanchi, K. G. Synthesis 1999, 760.
8. (c) Chaudhari, S. S.; Akamanchi, K. G. Tetrahedron Lett. 1998, 39, 3209.
9. (d) Salgaonkar, P. D.; Shukla, V. G., Akamanchi, K. G. Aust. J. Chem., communicated.
10. Shukla, V. G.; Salgaonkar, P. D.; Akamanchi, K. G. J. Org. Chem. 2003, 68, 5422.
11. (a) Wu, Y.; Shen, X.; Huang, J.-H.; Tang, C-J.; Liu, H.-H.; Hu, Q. Tetrahedron Lett. 2002, 43, 6443.
12. (b) Srilakshmi Krishnaveni, N.; Surendra, K.; Nageswar, Y. V. D.; Rama Rao, K. Synthesis 2003, 2295.
13. (c) Barton, D. H. R.; Godfrey, C. R. A.; Morzycki, J. W.; Motherwell, W. B.; Stobie, A. Tetrahedron Lett. 1982, 23, 957.
14. (d) Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 287.
15. (a) Larsen, L.; Garner, D. C.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1989, 2311.
16. (b) Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synlett 1999, 413; and references cited therein.
17. (a) Chen, C. H. Tetrahedron Lett. 1976,1, 25.
18. (b) Chen, C. H.; Donatelli, B. A. J. Org. Chem. 1976, 41, 3053.
19. (c) Janssen, J. W. A. M.; Kwart, H. J. Org. Chem. 1977, 42, 1530.
20. Yoshino, H.; Kawazoe, Y.; Taguchi, T. Synthesis 1974, 713.
21. Karimi, B.; Hazarkhani, H. Synthesis 2003, 2547.
22. Francisco, C. G.; Freire, R.; Hernandez, R.; Salazar, J. A.; Suarez, E. Tetrahedron Lett. 1984, 25, 1621.
23. (a) Tani, H.; Inamasu, T.; Tamura, R.; Suzuki, H. Chem. Lett. 1990, 1323.
24. (b) Tani, H.; Inamasu, T.; Masumoto, K.; Tamura, R.; Shimizu, H.; Suzuki, H. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 67, 261.
25. Ong, B. S. Tetrahedron Lett. 1980, 21, 4225.
26. 4 and concentrated in vacuo. Purification by silica gel column chromatography (10% EtOAc-hexane) afforded the pure dihydro-1,4-dithiins and dihydro-1,4-dithianes.