Formation of substituted macrocyclic ethers by radical cyclisation

Chemical Communications

Volumn , Issue 5, 1997, Pages 499-500

  Beckwith, Athelstan L J ^a   Drok, Kitty ^a   Maillard, Bernard ^b   Degueil Castaing, Marie ^b   Philippon, Annie ^b  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001776007     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a608494j     Document Type: Short Survey

References (16)

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2. A. L. J. Beckwith, V. W. Bowry and G. Moad, J. Org. Chem., 1988, 53, 1632.
3. A. N. Abeywickrema and A. L. J. Beckwith, J. Chem. Soc., Chem. Commun., 1986, 464.
4. A. L. J. Beckwith and C. H. Schiesser, Tetrahedron, 1985, 41, 3925.
5. The monotosylate was prepared by the general method previously used for the preparation of the ditosylate: J. Dale and P. O. Kristiansen, Acta Chem. Scand., 1972, 26, 1471.
6. A. L. J. Beckwith and G. Moad, J. Chem. Soc., Chem. Commun., 1974, 472.
7. C. Chatgilialoglu, K. U. Ingold and J. C. Scaiano, J. Am. Chem. Soc., 1981, 103, 7739.
8. N. A. Porter and V. H.-T. Chang, J. Am. Chem. Soc., 1987, 109, 4976.
9. 2j was obtained via DCC coupling of mono tert-butyl maleate with tetraethylene glycol monotosylate. tert-Butyl maleate was prepared by the same general method as that previously used for the preparation of tert-butyl phthalate: W. A. Fessler and R. L. Schriner, J. Am. Chem. Soc., 1936, 58, 1384.
10. N. A. Porter, D. R. Magnin and B. T. Wright, J. Am. Chem. Soc., 1986, 108, 2787; N. A. Porter, B. Lacher, V. H.-T. Chang and D. R. Magnin, J. Am. Chem. Soc., 1989, 111, 8309.
11. N. A. Porter, D. R. Magnin and B. T. Wright, J. Am. Chem. Soc., 1986, 108, 2787; N. A. Porter, B. Lacher, V. H.-T. Chang and D. R. Magnin, J. Am. Chem. Soc., 1989, 111, 8309.
12. For some recent examples see: J. Ullrich and D. P. Curran, Tetrahedron Lett., 1995, 36, 8921; E. I. Troyansky, R. F. Ismagilov, V. V. Samoshin, Y. A. Strelenko, D. V. Demchuk, G. I. Nikishin, S. V. Lindeman, V. V. Khrustalyov and Y. T. Struchkov, Tetrahedron, 1995, 51, 11431; I. Ryu, K. Nagahara, H. Yamazaki, S. Tsunoi and N. Sonoda, Synlett, 1994, 643; M. J. Begley, G. Pattenden, A. J. Smithies and D. S. Walter, Tetrahedron Lett., 1994, 35, 2417; K. S. Feldman, H. M. Berven, A. L. Romanelli and M. Parvez, J. Org. Chem., 1993, 58, 6851.
13. For some recent examples see: J. Ullrich and D. P. Curran, Tetrahedron Lett., 1995, 36, 8921; E. I. Troyansky, R. F. Ismagilov, V. V. Samoshin, Y. A. Strelenko, D. V. Demchuk, G. I. Nikishin, S. V. Lindeman, V. V. Khrustalyov and Y. T. Struchkov, Tetrahedron, 1995, 51, 11431; I. Ryu, K. Nagahara, H. Yamazaki, S. Tsunoi and N. Sonoda, Synlett, 1994, 643; M. J. Begley, G. Pattenden, A. J. Smithies and D. S. Walter, Tetrahedron Lett., 1994, 35, 2417; K. S. Feldman, H. M. Berven, A. L. Romanelli and M. Parvez, J. Org. Chem., 1993, 58, 6851.
14. For some recent examples see: J. Ullrich and D. P. Curran, Tetrahedron Lett., 1995, 36, 8921; E. I. Troyansky, R. F. Ismagilov, V. V. Samoshin, Y. A. Strelenko, D. V. Demchuk, G. I. Nikishin, S. V. Lindeman, V. V. Khrustalyov and Y. T. Struchkov, Tetrahedron, 1995, 51, 11431; I. Ryu, K. Nagahara, H. Yamazaki, S. Tsunoi and N. Sonoda, Synlett, 1994, 643; M. J. Begley, G. Pattenden, A. J. Smithies and D. S. Walter, Tetrahedron Lett., 1994, 35, 2417; K. S. Feldman, H. M. Berven, A. L. Romanelli and M. Parvez, J. Org. Chem., 1993, 58, 6851.
15. For some recent examples see: J. Ullrich and D. P. Curran, Tetrahedron Lett., 1995, 36, 8921; E. I. Troyansky, R. F. Ismagilov, V. V. Samoshin, Y. A. Strelenko, D. V. Demchuk, G. I. Nikishin, S. V. Lindeman, V. V. Khrustalyov and Y. T. Struchkov, Tetrahedron, 1995, 51, 11431; I. Ryu, K. Nagahara, H. Yamazaki, S. Tsunoi and N. Sonoda, Synlett, 1994, 643; M. J. Begley, G. Pattenden, A. J. Smithies and D. S. Walter, Tetrahedron Lett., 1994, 35, 2417; K. S. Feldman, H. M. Berven, A. L. Romanelli and M. Parvez, J. Org. Chem., 1993, 58, 6851.
16. For some recent examples see: J. Ullrich and D. P. Curran, Tetrahedron Lett., 1995, 36, 8921; E. I. Troyansky, R. F. Ismagilov, V. V. Samoshin, Y. A. Strelenko, D. V. Demchuk, G. I. Nikishin, S. V. Lindeman, V. V. Khrustalyov and Y. T. Struchkov, Tetrahedron, 1995, 51, 11431; I. Ryu, K. Nagahara, H. Yamazaki, S. Tsunoi and N. Sonoda, Synlett, 1994, 643; M. J. Begley, G. Pattenden, A. J. Smithies and D. S. Walter, Tetrahedron Lett., 1994, 35, 2417; K. S. Feldman, H. M. Berven, A. L. Romanelli and M. Parvez, J. Org. Chem., 1993, 58, 6851.