Organomercury/aluminum-mediated acylative cleavage of cyclic ethers

Tetrahedron

Volumn 55, Issue 7, 1999, Pages 1851-1858

  Luzzio, Frederick A ^a   Bobb, Rhiana A ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

Author keywords

Acylation; Aluminum; Epoxides; Mercury

Indexed keywords

ALUMINUM DERIVATIVE; EPOXIDE; ETHER DERIVATIVE; ORGANOMERCURY COMPOUND; TETRAHYDROFURAN DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0033548206     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01226-5     Document Type: Article

References (30)

1. Ranu, B.C.; Bhar, S. Org. Prep. Proc. Int. 1996, 25, 371-409.
2. Bhatt, M.V; Kulkarni, S.U. Synthesis 1983, 249-282.
3. Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis, Wiley: New York, 1991; pp. 14- 15.
4. Bhar, S.; Ranu, B.C. J. Org. Chem. 1995, 60, 745-747.
5. Quian, C.; Qiu, A.; Huang, Y.; Chen, W. J. Organomet. Chem. 1991, 412, 53-59.
6. Iqbal, J.; Srivastava, R.R. Tetrahedron 1991, 47, 3155-3170.
7. Iqbal, J.; Khan, M.A.; Srivastava, R.R. Tetrahedron Lett. 1988, 39, 4985-4986.
8. Kotsuki, H.; Ichikawa, Y.; Nishizawa, H. Chem. Lett. 1988, 673-676.
9. Shibata, I.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1986, 27, 3021-3024.
10. Fitch, J.W.; Payne, W.G.; Westmoreland, D. J. Org. Chem. 1983, 48, 751-753.
11. Pri-Bar, I.; Stille, J.K. J. Org. Chem. 1982, 47, 1215-1220.
12. Alper, H.; Edward, J.T. Can. J. Chem. 1970, 48, 1623-1624.
13. Alper, H.; Huang, C.C. J. Org. Chem. 1973, 38, 64-71.
14. (a) Cloke, J.B.; Pilgrim, F.J. J. Am. Chem. Soc. 1939, 61, 2667-2669.
15. (b) Mimero, P.; Saluzzo, C.; Amouroux, R. Tetrahedron Lett. 1994, 35, 1553-1556.
16. Taniguchi, Y.; Tanaka, S.; Kitamura, T.; Fujiwara, Y. Tet. Lett. 1998, 39, 4559-4560.
17. Gros, P.; LePerchec, P. Senet, J.P. J. Org. Chem. 1994, 59, 4925-4930.
18. Henbest, H.B.; Nicholls, B. J. Chem. Soc. 1959, 227-236.
19. Chatt, J. Chem. Rev. 1951, 48, 7-43.
20. Brown, H.C.; Rei, M.H. J. Am. Chem. Soc. 1969, 91, 5646-5647.
21. trans-2-Chloromercuri-1-nitrocyclohexane (Bachman, G.B.; Whitehouse, M.C. J. Org. Chem. 1967, 32, 2303-2308) will also cleave tetrahydrofuran in the presence of aluminum; however the yields are low (<40%) and the products are accompanied by tars.
22. 2: Synerholm, M.E. Org. Synth.; Horning, E.C., Ed.; Wiley: New York, 1955; Collect. Vol. III, pp. 187-188.
23. Clive, D.L.J.; Beaulieu, P.L. J. Chem. Soc. Chem. Commun. 1983, 307-309.
24. Although ring strain may be the determining factor in the cleavage of epoxides, it may play a less important role in THF cleavage. Tetrahydropyran does not respond to the cleavage reaction under similar conditions to THF cleavage. The authors thank a referee for pertinent comments.
25. Larock, R.C. Angew. Chem. Int. Ed. Engl. 1978, 17, 27-37.
26. The formation and involvement of mixed aluminum alkoxide species would also be considered in this step.
27. 3 species by direct reaction of the aluminum metal/acid chloride and its involvement in the cleavage (Bobb, R., M.S. Dissertation, University of Louisville, 1997).
28. In terms of potential utility in organic synthesis, the acylative cleavage of meso-epoxides yields a mixture of haloesters, compounds which are useful substrates for enzymatic resolution: Fukazawa, T.; Hashimoto, T. Tetrahedron Asymmetry 1993, 4, 2323-2326.
29. The handling and disposal of mercury waste was done in accordance with the guidelines found in Prudent Practices in the Laboratory; National Academy Press, Washington, D.C., 1995, pp 166, 350-351.
30. Rolhoff, A. Chimia, 1985, 39, 392-393.