Synthesis 2002(15): 2266-2270
DOI: 10.1055/s-2002-34853
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Practical Synthesis of Benzocrown Ethers under Phase-Transfer Catalysis Conditions

Tatyana Bogaschenko, Stepan Basok, Catherine Kulygina, Alexander Lyapunov, Nikolay Lukyanenko*
A.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, 86 Lustdorfskaya doroga, Odessa 65080, Ukraine
Fax: +38(48)2652012; e-Mail: ngl@farlep.net;
Further Information

Publication History

Received 24 May 2002
Publication Date:
21 October 2002 (online)

Abstract

Convenient and effective procedures for the synthesis of benzo-12-crown-4, benzo-15-crown-5, benzo-18-crown-6, benzo-21-crown-7 and benzo-24-crown-8 under phase-transfer catalysis conditions have been developed.

    References

  • 1 Pedersen CJ. Angew. Chem. Int. Ed.  1988,  27:  1021 
  • 2 Vögtle F. Weber E. In The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulphur Analogues   Patai S. Wiley; Chichester: 1980.  p.59-156  
  • 3 Laidler DA. Stoddart JF. In The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulphur Analogues   Patai S. Wiley; Chichester: 1980.  p.1-58  
  • 4 Viout P. Lehn J.-M. Macrocyclic Chemistry   VCH; New York: 1993. 
  • 5 Vögtle F. Supramolecular Chemistry   Wiley; New York: 1991. 
  • 6 Lehn J.-M. Supramolecular Chemistry   VCH; New York: 1995. 
  • 7 Fyfe MCT. Stoddart JF. Adv. Supramol. Chem.  1999,  5:  1 
  • 8 Cantrill SJ. Pease AR. Stoddart JF. J. Chem. Soc., Dalton Trans.  2000,  3715 
  • 9 Amabilino DB. Stoddart JF. Chem. Rev.  1995,  95:  2725 
  • 10 Gokel GW. Chem. Soc. Rev.  1992,  21:  39 
  • 11 Gibson HW. Macromol. Chem. Phys.  2000,  201:  815 
  • 12 Kakuchi T. Watanabe T. Matsunami S. Kamimura H. Polymer  1997,  38:  1233 
  • 13 Knops P. Sendhoff N. Mekelburger H.-B. Vögtle F. Top. Curr. Chem.  1992,  161:  3 
  • 14 Ostrowicki A. Koepp E. Vögtle F. Top. Curr. Chem.  1992,  161:  39 
  • 15 Dehmlow EV. Dehmlow SS. Phase Transfer Catalysis   VCH; Weinheim: 1993. 
  • 16 Bogatsky AV. Lukyanenko NG. Basok SS. Ostrovskaya LK. Synthesis  1984,  138 
  • 17 Lukyanenko NG. Basok SS. Filonova LK. J. Chem. Soc., Perkin Trans. 1  1988,  3141 
  • 18 Hodgkinson LC. Sutherland IO. J. Chem. Soc., Perkin Trans. 1  1979,  1908 
  • 19 Topal G. Demire N. Togrul M. Turgut Y. Hosgoren H. J. Heterocycl. Chem.  2001,  38:  281 
  • 20 Weber E. Chem. Ber.  1985,  118:  4439 
  • 21 Draye M. Favre-Reguillon A. Chomel R. Faure R. Guy A. Foos J. Lemaire M. Bull. Soc. Chim. Fr.  1996,  133:  183 
  • 22 Kyba EP. Helheson RC. Madan K. Gokel GW. Tarnowski TL. Cram DG. J. Am. Chem. Soc.  1977,  99:  2564 
  • 23 Czech B. Czech A. Bartch RA. J. Heterocycl. Chem.  1984,  21:  341 
  • 24 Gokel GW. Korzeniowski SH. Macrocyclic Polyether Syntheses   Springer; Berlin: 1982. 
  • 25 Gibson HW. Bheda MC. Engen P. Shen YX. Sze H. Zhang H. Gibson MD. Delaviz Y. Lee S.-H. Liu S. Wang L. Nagvekar D. Rancourt J. Taylor LT. J. Org. Chem.  1994,  59:  2186 
  • 26 Ouchi M. Inoue Y. Kanzaki T. Hakushi T. J. Org. Chem.  1984,  49:  1408 
  • 27 Ouchi M. Inoue Y. Lu Y. Nagamune S. Nakamura S. Wada K. Hakushi T. Bull. Chem. Soc. Jpn.  1990,  63:  1260 
  • 28 Pedersen CJ. J. Am. Chem. Soc.  1967,  89:  7017