Trichloroisocyanuric acid, as an industrial chemical, promotes transthioacetalization of diacetals of 2,2-bis (hydroxymethyl)-1,3-propanediol and cleavage of thioacetals

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 177, Issue 11, 2002, Pages 2571-2577

  Firouzabadi, Habib ^a   Iranpoor, Nasser ^a   Hazarkhani, Hassan ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Deprotection; Diacetals of 2,2 bis (hydroxymethyl) 1,3 propanediol; Thioacetals; Transthioacetalization; Trichloroisocyanuric acid

Indexed keywords

ACETAL DERIVATIVE; INDUSTRIAL CHEMICAL; PROPANEDIOL DERIVATIVE; SILICA GEL; SYMCLOSENE; THIOACETALDEHYDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; DEPROTECTION REACTION; HYDROLYSIS; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 0036861232     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426500214566     Document Type: Article

References (47)

1. B. T. Grobel and D. Seebach, Synthesis, 357 (1977).
2. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis (Wiley: New York, 1991), 2nd ed., pp. 178-207.
3. E. J. Corey and D. Seebach, Angew. Chem., Int. Ed. Engl., 4, 1075, 1077 (1965).
4. D. Seebach, Angew. Chem., Int. Ed. Engl., 8, 639 (1969).
5. J. H. Park and S. Kim, Chem. Lett., 629 (1989).
6. H. Tani, K. Masumoto, T. Inamasu, and H. Suzuki, Tetrahedron Lett., 32, 2039 (1991).
7. V. G. Saraswathy and S. Sankararaman, J. Org. Chem., 59, 4665 (1994).
8. H. Firouzabadi, N. Iranpoor, and B. Karimi, Synlett., 739 (1998).
9. G. K. Jnaneshwara, N. B. Barhate, A. V. H. Sudalai, Deshpande, R. D. Wakharkarq A. S. Gajare, M. S. Shingare, and R. Sukumar, J. Chem. Soc., Perkin Trans., 1, 965 (1998).
10. H. Firouzabadi, N. Iranpoor, and B. Karimi, Synlett., 319 (1999).
11. Firouzabadi, N. Iranpoor, and B. Karimi, Synthesis, 58-60 (1999).
12. H. Firouzabadi, B. Karimi, and S. Eslami, Tetrahedron Lett., 4055-4058 (1999).
13. H. Firouzabadi, N. Iranpoor, H. Hazarkhani, and B. Karimi, J. Org. Chem., 66, 7527 (2001).
14. H. Firouzabadi, N. Iranpoor, and B. Karimi, Synlett., 321 (1999).
15. D. J. Kalita, R. Borah, and C. Sarma, Tetrahedron Lett., 39, 4573 (1998).
16. R. Ballini, G. Bosiva, B. Frullanti, R. Maggi, G. Sartori, and F. Schroer, Tetrahedron Lett., 39, 1615 (1998).
17. M. T. S. Jin, T. S. Li, Z. H. Zhang, and Y. J. Yuan, Synth. Commun., 1601 (1999).
18. C. D. Wang, X. Z. Shi, and R. J. Xie, Synth. Commun., 2517 (1997).
19. X. Chen, Y. T. Xu, and C. X. Jin, Hecheng Huaxue, 5, 212 (1997).
20. E. Bograchov, J. Am. Chem. Soc., 72, 2265 (1950).
21. Y. Peng, G. Song, and X. Qian, Synth. Commun., 31, 3735 (2001).
22. K. Ziegler et al., Justus Liebigs Ann. Chem., 80 (1942).
23. E. C. Juenge, P. L. Spangler, and W. P. Duncan, J. Org. Chem., 31, 3836 (1966).
24. E. C. Juenge and D. A. Beal, Tetrahedron Lett., 5819 (1968).
25. E. C. Juenge, D. A. Beal, and W. P. Duncan, J. Org. Chem., 35, 719 (1970).
26. G. A. Olah, S. C. Narang, and G. F. Salem, Synthesis, 659 (1980).
27. G. A. Hiegel, J. Ramirez, and R. K. Barr, Synth. Commun., 29, 1415 (1999).
28. Z. X. Xiong, N. P. Huang, and P. Zhong, Synth. Commun., 245 (2001).
29. P. Zhong and M. P. Guo, Synth. Commun., 1825 (2001).
30. P. Zhong and M. P. Guo, Synth. Commun., 1507 (2001).
31. H. Firouzabadi, N. Iranpoor, B. Karimi, and H. Hazarkhani, Synlett., 263 (2001).
32. K. Saigo, Y. Hashimoto, and N. Kihara, Chemistry Lett., 831 (1990).
33. N. Komatsu, A. Taniguchi, M. Uda, and H. Suzuki, Chem. Commun., 1847 (1996).
34. S. A. Haroutounian, Synthesis, 39 (1995).
35. N. J. Cussans and S. V. Ley, J. Chem. Soc. Perkin Trans. I, 1654 (1980).
36. M. Schmittel and M. Levis, Synlett., 315 (1996).
37. M. Kamata, H. Otogawa, and E. Hasegawa, Tetrahedron Lett., 32, 7421 (1991).
38. A. S. Kiselyov and L. Strekwski, Tetrahedron, 49, 2151 (1993).
39. M. Curini, M. C. Marcotullio, E. Pisani, and O. Rosati, Synlett., 769 (1997).
40. M. Balogh, A. Cornélis, and P. Laszlo, Tetrahedron Lett., 25, 3313 (1984).
41. H. M. Meshram, G. S. Reddy, and J. S. Yadav, Tetrahedron Lett., 38, 8891 (1997).
42. G. Mehta and R. Uma, Tetrahedron Lett., 37, 1897 (1996).
43. B. P. Bandgar and S. P. Kasture, Green Chemistry, 2, 154 (2000).
44. A. K. Banerjee and M. S. Laya, Russ. Chem Rev., 69, 947 (2000).
45. G. A. Olah, S. C. Narang, and G. F. Salem, Synthesis, 659 (1980).
46. H. Firouzabadi, N. Iranpoor, and B. Karimi, Synlett., 413 (1999).
47. Handbook of Chemistry and Physics, (Chemical Rubber Company, Cleveland, OH, 1973-74), 5th ed.