A novel one-pot conversion of 2-naphthols into 1,1′-binaphthalene-2,2′-diols

Synthetic Communications

Volumn 26, Issue 13, 1996, Pages 2597-2601

  Holý, Petr ^a   Bělohradský, Martin ^a   Závada, Jiří ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE; NAPHTHOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029973174     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608004572     Document Type: Article

References (13)

1. (a) Trost, B.M. Pure Appl. Chem. 1992, 64, 315.
2. (b) Kagan, H.B. and Riant, O. Chem. Rev. 1992, 92, 1007.
3. Pummerer, R.; Rieche, A. and Prell, E. Chem. Ber. 1926, 59, 2159. Toda, F.; Tanaka, K. and Iwata, S. J. Org. Chem. 1989, 54, 3007.
4. Pummerer, R.; Rieche, A. and Prell, E. Chem. Ber. 1926, 59, 2159. Toda, F.; Tanaka, K. and Iwata, S. J. Org. Chem. 1989, 54, 3007.
5. (a) Feringa, B. and Wynberg, H. Tetrahedron Lett. 1977, 4447.
6. (b) Brussee, J.; Groenendijk, J.L.G.; te Koppele, J.M. and Jansen, A.C. Tetrahedron 1986, 41, 3313.
7. Dewar, M.J.S. and Nakaya, T. J. Am. Chem. Soc. 1988, 90, 7134.
8. Vogel, A. I. "Vogel's textbook of practical organic chemistry", 5th ed./rev. by Furniss, B.S.; Hannaford, P.W.G.; Smith, A.R. and Tatchell, A.R.,: Longmann, England, 1989; p. 838.
9. Bělohradský, M.; Holý, P. and Závada, J. J. Chem. Soc. Perkin Trans. 2, 1995, 1853.
10. Significantly, the 1:2 bromine:2-naphthoxide stoichiometry employed in the novel procedure suppresses effectively the formation of higher brominated by-products arising in the preparation of 1-bromo-2-naphthol by a routine bromination.
11. 6). In order to achieve a complete conversion of 1a in the overall reaction, it is accordingly recommended to increase the calculated amount of bromine by about 10%.
12. Sakamoto, T.; Yonehara, H. and Pac, C. J. Org. Chem. 1994, 59, 6859.
13. Rieker, A.; Zeller, N.; Schurr K. and Müller, E. Liebigs Ann. Chem. 1966, 697, 1.