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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 13
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Original Articles

A Novel One-Pot Conversion of 2-Naphthols into 1,1′-Binaphthalene-2,2′-Diols

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Pages 2597-2601 | Received 19 Jan 1996, Published online: 23 Aug 2006

References

  • Trost , B. M. 1992 . Pure Appl. Chem. , 64 : 315
  • Kagan , H. B. and Riant , O. 1992 . Chem. Rev. , 92 : 1007
  • Pummerer , R. , Rieche , A. and Prell , E. 1926 . Chem. Ber. , 59 : 2159
  • Toda , F. , Tanaka , K. and Iwata , S. 1989 . J. Org. Chem. , 54 : 3007
  • Feringa , B. and Wynberg , H. 1977 . Tetrahedron Lett. , : 4447
  • Brussee , J. , Groenendijk , J. L.G. , te Koppele , J. M. and Jansen , A. C. 1986 . Tetrahedron , 41 : 3313
  • Dewar , M. J.S. and Nakaya , T. 1988 . J. Am. Chem. Soc. , 90 : 7134
  • Vogel , A. I. 1989 . Vogel's textbook of practical organic chemistry , 5th ed./rev. , Edited by: Furniss , B. S. , Hannaford , P. W.G. , Smith , A. R. and Tatchell , A. R. 838 England : Longmann .
  • Bělohradský , M. , Holý , P. and Závada , J. 1995 . J. Chem. Soc. Perkin Trans. , 2 : 1853
  • 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
  • Concurrently with the dominant (95%) cross-coupling between 1a and 2a, a minor self-coupling reaction of 2a takes place (ref.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%
  • Sakamoto , T. , Yonehara , H. and Pac , C. 1994 . J. Org. Chem. , 59 : 6859
  • Rieker , A. , Zeller , N. , Schurr , K. and Müller , E. 1966 . Liebigs Ann. Chem. , 697 : 1

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