Convenient tetrahydropyranylation of alcohols and phenols by catalytic ferric sulfate hydrate (Fe2(SO4)3· xH2O)

Canadian Journal of Chemistry

Volumn 83, Issue 8, 2005, Pages 1120-1123

  Li, Lingjun ^a   Zhu, Lizhi ^b   Zhang, Xinying ^a   Zhang, Guisheng ^a   Qu, Guirong ^a  

^a HENAN NORMAL UNIVERSITY   (China)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

Ferric sulfate hydrate; Green chemistry; Selective monotetrahydropyranylation; Tetrahydropyranylation

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; ETHERS; HYDRATES; PHENOLS; REACTION KINETICS;

DIOLS; SELECTIVE MONOTETRAHYDROPYRANYLATION; TETRAHYDROPYRANYLATION;

ALCOHOLS;

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; FERRIC SULFATE; PHENOL DERIVATIVE; TETRAHYDROPYRANYL ETHER;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; CHEMICAL REACTION; DEPROTECTION REACTION; ENVIRONMENTAL TEMPERATURE; REACTION ANALYSIS; STEREOCHEMISTRY; TETRAHYDROPYRANYLATION;

EID: 28944435012     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-136     Document Type: Article

References (22)

1. (a) T.W. Greene and P.G.M. Wuts (Editors). Protective groups in organic synthesis. 3rd ed. John Wiley and Sons, New York. 1999;
2. (b) S. Hoyer and P. Laszlo. Synthesis, 655 (1986)
3. (c) P.J. Kocienski (Editor). Protecting groups. Thieme, Stuttgart. 1994.
4. M. Miyashita, A. Yoshikoshi, and P.A. Grieco. J. Org. Chem. 42, 3772 (1977).
5. K. Tanemura, T. Horaguchi, and T. Suzuki. Bull. Chem. Soc. Jpn. 65, 4583 (1992).
6. H. Alper and L. Dinkes. Synthesis, 81 (1972).
7. V. Bolitt, C. Mioskowski, D.S. Shin, and J.R. Falck. Tetrahedron Lett. 29, 4583 (1988).
8. S. Ma and L.M. Venanzi. Tetrahedron Lett. 34, 5269 (1993).
9. N. Deka and J.C. Sarma. Synth. Commun. 30, 4435 (2000).
10. L.C. Branco and C.A.M. Afonso. Tetrahedron Lett. 57, 4405 (2001).
11. B. Karimi and M. Jafar. Tetrahedron Lett. 43, 5353 (2002).
12. T. Mineno. Tetrahedron Lett. 43, 7975 (2002).
13. S. Palaniappan, M.S. Ram, and C. A. Amarnath. Green Chem. 4, 369 (2002).
14. G.P. Romanelli, G. Baronetti, H.J. Thamas, and J.C. Autino. Tetrahedron Lett. 43, 7589 (2002).
15. T. Nishiguchi, K. Kawamine, and T.J. Ohtsuka. J. Chem. Soc. Perkin Trans, 1, 153 (1992).
16. N. Deka and J.C. Sarma. J. Org. Chem. 66, 1947 (2001).
17. V.V. Namboodiri and R.S. Varma. Chem. Commun. 342 (2002).
18. (a) G. Zhang and H. Gong. Synth. Commun. 29, 1547 (1999);
19. (b) G. Zhang. Synth. Commun. 29, 607 (1999).
20. X. Zhang, L. Li, and G. Zhang. Green Chem. 5, 646 (2003).
21. (a) M. Schwarz and R.M. Waters. Synthesis, 567 (1972);
22. (b) S. Chandrasekhar, T. Ramachandar, M. Venkat Reddy, and M. Takhi. J. Org. Chem. 65, 4729 (2000).