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Języki publikacji
Abstrakty
A series of new 2-aryloxymethyloxiranes prepared from epichlorohydrin and substituted phenols was subjected to nucleophilic opening of the oxiranering. A comparison of regioselectivity and product yield for oxirane cleavage by means of aqueous hydrohalogenic acids or lithium tetrahalogenocuprates under an hydrous conditions was performed. The latter method provided very high regioselectivity for 3-aryloxy-1-halogeno propan-2-ols as well as excellent yields.
Wydawca
Czasopismo
Rocznik
Tom
Strony
595--604
Opis fizyczny
Bibliogr. 21 poz., rys.
Twórcy
autor
autor
autor
- Institute of General Food Chemistry, Łódź University of Technology, ul. Stefanowskiego 4/10, 90-924 Łódź, Poland, maciejmaciejewski1980@tlen.pl
Bibliografia
- 1. Faulkner D.J., Nat. Prod. Rep., 25, 551 (1984).
- 2. Bevinakatti H.S. and Banerji A.A., J. Org. Chem., 57, 6003 (1992).
- 3. Ader U. and Schneider M.P., Tetrahedron: Asymmetry, 3, 201 (1992).
- 4. Ader U. and Schneider M.P., Tetrahedron: Asymmetry, 3, 205 (1992).
- 5. Bartlett P.A., Asymmetric Synthesis, vol. 3, Morrison J.D. Ed., Academic Press Inc., New York 1984, 411-454.
- 6. Moen A.R, Karstad R. and Anthonsen T, Biocatal. Biotrans., 23, 45 (2005).
- 7. Sharghi H. and Naeimi H., Bull. Chem. Soc. Japan, 72, 1525 (1999).
- 8. Coxon J.N., Hartshorn M.R and Rae W.J., Tetrahedron, 26, 1091 (1970).
- 9. Sharghi H. and Eskandari M.M., Tetrahedron, 59, 8509 (2003).
- 10. Sabitha G., Babu R.S., Rajkumar M., Reddy C.S. and Yadav J.S., Tetrahedron Lett., 42, 3955 (2001).
- 11. Kotsuki H, Shimanouchi T, Ohshima R. and Fujiwara S., Tetrahedron, 54, 2709 (1998).
- 12. Reddy M.A., Surendra K., Bhanumathi N. and Rao K.R., Tetrahedron, 58, 6003 (2002).
- 13. Kotsuki H. and Shimanouchi T, Tetrahedron Lett, 37, 1845 (1996).
- 14. Das B., Krishnaiah M. and Venkateswarlu K., Tetrahedron Lett., 47,4457 (2006).
- 15. Sharghi H, Eskandari M.M. and Ghavami R., J. Mol. Catal. A, 215, 55 (2004).
- 16. Tamura M. and Kochi J.K., Synthesis, 303 (1972).
- 17. Kawakami Y. and Yamashita Y, J. Org. Chem., 48, 1912 (1983).
- 18. Wesełucha-Birczyńska A., Oleksyn B.J., Hoffmann S.K., Śliwiński J., Borzęcka-Prokop B., Goslar J. and Hilczer W., Inorg. Chem., 40, 4526 (2001).
- 19. Pinchuk V.M., Plakhotnik A.V. and Pinchuk TV., J. Struct. Chem., 35, 122 (1994).
- 20. Ciaccio J.A., Addes K.J. and Bell T.W., Tetrahedron Lett., 27, 3697 (1986).
- 21. Dawe R.D., Molinski T.F. and Turner J.V., Tetrahedron Lett., 25, 2061 (1984).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ7-0015-0009