Immediate and efficient oxidative deprotection of dithioacetals to carbonyl compounds by zinc dichromate trihydrate (ZnCr2O7 · 3H2O)

Synthetic Communications

Volumn 34, Issue 11, 2004, Pages 1967-1972

  Firouzabadi, Habib ^a   Iranpoor, Nasser ^a   Hassani, Hassan ^a   Sobhani, Sara ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

1,3 Dithianes; 1,3 Dithiolanes; Carbonyl compounds; Dibutyl dithioacetals; Oxidative deprotection; Thioacetals; Zinc dichromate trihydrate

Indexed keywords

1,3 DITHIANE DERIVATIVE; 1,3 DITHIOLANE DERIVATIVE; ACETAL; CARBONYL DERIVATIVE; DIBUTYLDITHIOACETAL; DICHROMATE ZINC; DITHIOACETAL; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; OXIDATION; ROOM TEMPERATURE;

EID: 2942644429     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120037908     Document Type: Article

References (21)

1. Vogel's Textbook of Practical Organic Chemistry, 5th Ed.; Longman: Harlow, 1989; 787.
2. (a) Kociencki, P.J. Protecting Groups; Thieme: New York, 1994;
3. (b) Corey, E.J.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1965, 4, 1075;
4. (c) Seebach, D. Angew. Chem. Int. Ed. Engl. 1969, 8, 639;
5. (d) Grobel, B.T.; Seebach, D. Synthesis 1977, 357;
6. (e) Bulman Page, P.C.; Van Niel, M.B.; Prodger, J.C. Tetrahedron 1989, 45, 7643;
7. (f) Tietze, L.F.; Weigand, B.; Wulff, C. Synthesis 2000, 69.
8. (a) Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis, 2nd Ed.; Wiley: New York, 1991; 198-207;
9. (b) Uemura, M.; Nishimura, H.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1991, 113, 5402;
10. (c) Ho, T.L.; Ho, H.C.; Wong, C.M. J. Chem. Soc. Chem. Commun. 1972, 791;
11. (d) Epling, G.A.; Wang, Q. Tetrahedron Lett. 1992, 33, 5909;
12. (e) Kamata, M.; Otogawa, H.; Hasegawa, E. Tetrahedron Lett. 1991, 32, 7421;
13. (f) Kamata, M.; Murakami, Y.; Tamagawa, Y.; Kato, M.; Hasegawa, E. Tetrahedron 1994, 50, 12821;
14. (g) Porter, Q.N.; Utley, J.H.P. J. Chem. Soc. Chem. Commun. 1978, 255;
15. (h) Gourey, J.; Martigny, P.; Simonet, J.; Jeminet, G. Tetrahedron 1981, 37, 1495;
16. (i) Barhate, N.B.; Shinde, P.D.; Mahajan, V.A.; Wakharkar, R.D. Tetrahedron Lett. 2002, 43, 6031;
17. (j) Banerjee, A.K.; Laya, M.S. Russ. Chem. Rev. 2000, 69, 947.
18. Wolf, S.; Ingold, C.F. J. Am. Chem. Soc. 1983, 105, 7755.
19. (a) Firouzabadi, H.; Sardarian, A.R.; Moosavipour, H.; Afshari, G.M. Synthesis 1986, 285;
20. (b) Firouzabadi, H.; Iranpoor, N.; Sobhani, S.; Sardarian, A.R. Tetrahedron Lett. 2001, 42, 4369.
21. Handbook of Table of Organic Compounds Identification, 3rd Ed.; CRC Press: 1967.