Syntheses of ligands containing two and three 2,2'-(bisamino)diphenyl ether units designed for molecular self-assembly on lithiation

Synthesis

Volumn , Issue 8, 1996, Pages 930-940

  Ashton, Peter R ^a   Hörner, Bernd ^a   Kocian, Oldrich ^a   Menzer, Stephan ^b   White, Andrew J P ^b   Stoddart, J Fraser ^a   Williams, David J ^b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

2,2' (bisamino)diphenyl ether; lithium amides; self assembly

Indexed keywords

DIPHENYL ETHER DERIVATIVE; ETHER DERIVATIVE; LIGAND; POLYAMINE;

ARTICLE; CRYSTALLOGRAPHY; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 0029830734     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4319     Document Type: Article

References (29)

1. For reviews of organolithium structural chemistry, including amidolithium species, see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Setzer, N. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624. Seebach, D. Proc. Robert A. Welch Found. Conf. Chem. Res. 1984, 27, 93. Boche, G. Angew. Chem. Int. Ed. Engl. 1989, 28, 211. Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929. Olsher, U.; Izatt, R. M.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137. Fieser, M. in Reagents for Organic Synthesis, Vol. 15; Wiley: New York, 1990.
2. For reviews of organolithium structural chemistry, including amidolithium species, see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Setzer, N. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624. Seebach, D. Proc. Robert A. Welch Found. Conf. Chem. Res. 1984, 27, 93. Boche, G. Angew. Chem. Int. Ed. Engl. 1989, 28, 211. Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929. Olsher, U.; Izatt, R. M.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137. Fieser, M. in Reagents for Organic Synthesis, Vol. 15; Wiley: New York, 1990.
3. For reviews of organolithium structural chemistry, including amidolithium species, see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Setzer, N. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624. Seebach, D. Proc. Robert A. Welch Found. Conf. Chem. Res. 1984, 27, 93. Boche, G. Angew. Chem. Int. Ed. Engl. 1989, 28, 211. Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929. Olsher, U.; Izatt, R. M.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137. Fieser, M. in Reagents for Organic Synthesis, Vol. 15; Wiley: New York, 1990.
4. For reviews of organolithium structural chemistry, including amidolithium species, see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Setzer, N. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624. Seebach, D. Proc. Robert A. Welch Found. Conf. Chem. Res. 1984, 27, 93. Boche, G. Angew. Chem. Int. Ed. Engl. 1989, 28, 211. Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929. Olsher, U.; Izatt, R. M.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137. Fieser, M. in Reagents for Organic Synthesis, Vol. 15; Wiley: New York, 1990.
5. For reviews of organolithium structural chemistry, including amidolithium species, see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Setzer, N. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624. Seebach, D. Proc. Robert A. Welch Found. Conf. Chem. Res. 1984, 27, 93. Boche, G. Angew. Chem. Int. Ed. Engl. 1989, 28, 211. Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929. Olsher, U.; Izatt, R. M.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137. Fieser, M. in Reagents for Organic Synthesis, Vol. 15; Wiley: New York, 1990.
6. For reviews of organolithium structural chemistry, including amidolithium species, see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Setzer, N. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624. Seebach, D. Proc. Robert A. Welch Found. Conf. Chem. Res. 1984, 27, 93. Boche, G. Angew. Chem. Int. Ed. Engl. 1989, 28, 211. Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929. Olsher, U.; Izatt, R. M.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137. Fieser, M. in Reagents for Organic Synthesis, Vol. 15; Wiley: New York, 1990.
7. For reviews of organolithium structural chemistry, including amidolithium species, see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Setzer, N. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624. Seebach, D. Proc. Robert A. Welch Found. Conf. Chem. Res. 1984, 27, 93. Boche, G. Angew. Chem. Int. Ed. Engl. 1989, 28, 211. Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929. Olsher, U.; Izatt, R. M.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137. Fieser, M. in Reagents for Organic Synthesis, Vol. 15; Wiley: New York, 1990.
8. For reviews of organolithium structural chemistry, including amidolithium species, see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Setzer, N. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624. Seebach, D. Proc. Robert A. Welch Found. Conf. Chem. Res. 1984, 27, 93. Boche, G. Angew. Chem. Int. Ed. Engl. 1989, 28, 211. Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929. Olsher, U.; Izatt, R. M.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137. Fieser, M. in Reagents for Organic Synthesis, Vol. 15; Wiley: New York, 1990.
9. For reviews of organolithium structural chemistry, including amidolithium species, see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Setzer, N. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Seebach, D. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624. Seebach, D. Proc. Robert A. Welch Found. Conf. Chem. Res. 1984, 27, 93. Boche, G. Angew. Chem. Int. Ed. Engl. 1989, 28, 211. Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929. Olsher, U.; Izatt, R. M.; Bradshaw, J. S.; Dalley, N. K. Chem. Rev. 1991, 91, 137. Fieser, M. in Reagents for Organic Synthesis, Vol. 15; Wiley: New York, 1990.
10. Cragg-Hine, I.; Davidson, M. G.; Kocian, O.; Mair, F. S.; Pohl, E.; Raithby, P. R.; Snaith, R.; Spencer, N.; Stoddart, J. F. Angew. Chem. Int. Ed. Engl. 1993, 32, 1182.
11. Cragg-Hine, I.; Davidson, M. G.; Kocian, O.; Kottke, T.; Mair, F. S.; Snaith, R.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1993, 1355.
12. Kocian, O.; Spencer, N.; Stoddart, J. F.; Cragg-Hine, I.; Davidson, M. G.; Mair, F. S.; Raithby, P. R.; Snaith, R. Tetrahedron 1994, 51, 579.
13. For the syntheses of polyamines, diamino- and polyamino ethers, azacrown ethers, and related compounds, see: Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. in Aza-Crown Macrocycles; Wiley: New York, 1993. Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. Tetrahedron 1992, 48, 4475. Gokel, G. W.; Dishong, D. M.; Schultz, R. A.; Gatto, V. J. Synthesis 1982, 997. Gokel, G. W.; Korzeniowski, S. H. in Macrocyclic Polyether Syntheses; Springer: Berlin, 1982. Weber, E.; Toner, J. L.; Goldberg, I.; Vögtle, F.; Laidler, D. A.; Stoddart, J. F.; Bartsch, R. A.; Liotta, C. L. in Crown Ethers and Analogs; Patai, S.; Rappoport, Z.; Eds.; Wiley: New York, 1989. Dietrich, B.; Viout, P.; Lehn, J.-M. in Macrocyclic Chemistry; VCH: Weinheim, 1992.
14. For the syntheses of polyamines, diamino- and polyamino ethers, azacrown ethers, and related compounds, see: Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. in Aza-Crown Macrocycles; Wiley: New York, 1993. Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. Tetrahedron 1992, 48, 4475. Gokel, G. W.; Dishong, D. M.; Schultz, R. A.; Gatto, V. J. Synthesis 1982, 997. Gokel, G. W.; Korzeniowski, S. H. in Macrocyclic Polyether Syntheses; Springer: Berlin, 1982. Weber, E.; Toner, J. L.; Goldberg, I.; Vögtle, F.; Laidler, D. A.; Stoddart, J. F.; Bartsch, R. A.; Liotta, C. L. in Crown Ethers and Analogs; Patai, S.; Rappoport, Z.; Eds.; Wiley: New York, 1989. Dietrich, B.; Viout, P.; Lehn, J.-M. in Macrocyclic Chemistry; VCH: Weinheim, 1992.
15. For the syntheses of polyamines, diamino- and polyamino ethers, azacrown ethers, and related compounds, see: Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. in Aza-Crown Macrocycles; Wiley: New York, 1993. Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. Tetrahedron 1992, 48, 4475. Gokel, G. W.; Dishong, D. M.; Schultz, R. A.; Gatto, V. J. Synthesis 1982, 997. Gokel, G. W.; Korzeniowski, S. H. in Macrocyclic Polyether Syntheses; Springer: Berlin, 1982. Weber, E.; Toner, J. L.; Goldberg, I.; Vögtle, F.; Laidler, D. A.; Stoddart, J. F.; Bartsch, R. A.; Liotta, C. L. in Crown Ethers and Analogs; Patai, S.; Rappoport, Z.; Eds.; Wiley: New York, 1989. Dietrich, B.; Viout, P.; Lehn, J.-M. in Macrocyclic Chemistry; VCH: Weinheim, 1992.
16. For the syntheses of polyamines, diamino- and polyamino ethers, azacrown ethers, and related compounds, see: Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. in Aza-Crown Macrocycles; Wiley: New York, 1993. Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. Tetrahedron 1992, 48, 4475. Gokel, G. W.; Dishong, D. M.; Schultz, R. A.; Gatto, V. J. Synthesis 1982, 997. Gokel, G. W.; Korzeniowski, S. H. in Macrocyclic Polyether Syntheses; Springer: Berlin, 1982. Weber, E.; Toner, J. L.; Goldberg, I.; Vögtle, F.; Laidler, D. A.; Stoddart, J. F.; Bartsch, R. A.; Liotta, C. L. in Crown Ethers and Analogs; Patai, S.; Rappoport, Z.; Eds.; Wiley: New York, 1989. Dietrich, B.; Viout, P.; Lehn, J.-M. in Macrocyclic Chemistry; VCH: Weinheim, 1992.
17. For the syntheses of polyamines, diamino- and polyamino ethers, azacrown ethers, and related compounds, see: Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. in Aza-Crown Macrocycles; Wiley: New York, 1993. Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. Tetrahedron 1992, 48, 4475. Gokel, G. W.; Dishong, D. M.; Schultz, R. A.; Gatto, V. J. Synthesis 1982, 997. Gokel, G. W.; Korzeniowski, S. H. in Macrocyclic Polyether Syntheses; Springer: Berlin, 1982. Weber, E.; Toner, J. L.; Goldberg, I.; Vögtle, F.; Laidler, D. A.; Stoddart, J. F.; Bartsch, R. A.; Liotta, C. L. in Crown Ethers and Analogs; Patai, S.; Rappoport, Z.; Eds.; Wiley: New York, 1989. Dietrich, B.; Viout, P.; Lehn, J.-M. in Macrocyclic Chemistry; VCH: Weinheim, 1992.
18. For the syntheses of polyamines, diamino- and polyamino ethers, azacrown ethers, and related compounds, see: Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. in Aza-Crown Macrocycles; Wiley: New York, 1993. Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. Tetrahedron 1992, 48, 4475. Gokel, G. W.; Dishong, D. M.; Schultz, R. A.; Gatto, V. J. Synthesis 1982, 997. Gokel, G. W.; Korzeniowski, S. H. in Macrocyclic Polyether Syntheses; Springer: Berlin, 1982. Weber, E.; Toner, J. L.; Goldberg, I.; Vögtle, F.; Laidler, D. A.; Stoddart, J. F.; Bartsch, R. A.; Liotta, C. L. in Crown Ethers and Analogs; Patai, S.; Rappoport, Z.; Eds.; Wiley: New York, 1989. Dietrich, B.; Viout, P.; Lehn, J.-M. in Macrocyclic Chemistry; VCH: Weinheim, 1992.
19. Wilshire, J. F. K. Aust. J. Chem. 1988, 41, 995.
20. Hoegberg, S. A.; Cram, D. J. J. Org. Chem. 1975, 40, 151.
21. Dietrich, B.; Lehn, J.-M.; Sauvage, J. P. Tetrahedron Lett. 1969, 2885. Dietrich, B.; Lehn, J.-M.; Sauvage, J. P.; Blanzat, J. Tetrahedron 1973, 29, 1629. Miyazaki, M.; Shimoishi, Y.; Miyata, H.; Tôei, K. J. Inorg. Nucl. Chem. 1974, 36, 2033. Ammann, D.; Bissig, R.; Güggi, M.; Pretsch, E.; Simon, W.; Borowitz, I. J.; Weiss, L. Helv. Chim. Acta 1975, 58, 1535.
22. Dietrich, B.; Lehn, J.-M.; Sauvage, J. P. Tetrahedron Lett. 1969, 2885. Dietrich, B.; Lehn, J.-M.; Sauvage, J. P.; Blanzat, J. Tetrahedron 1973, 29, 1629. Miyazaki, M.; Shimoishi, Y.; Miyata, H.; Tôei, K. J. Inorg. Nucl. Chem. 1974, 36, 2033. Ammann, D.; Bissig, R.; Güggi, M.; Pretsch, E.; Simon, W.; Borowitz, I. J.; Weiss, L. Helv. Chim. Acta 1975, 58, 1535.
23. Dietrich, B.; Lehn, J.-M.; Sauvage, J. P. Tetrahedron Lett. 1969, 2885. Dietrich, B.; Lehn, J.-M.; Sauvage, J. P.; Blanzat, J. Tetrahedron 1973, 29, 1629. Miyazaki, M.; Shimoishi, Y.; Miyata, H.; Tôei, K. J. Inorg. Nucl. Chem. 1974, 36, 2033. Ammann, D.; Bissig, R.; Güggi, M.; Pretsch, E.; Simon, W.; Borowitz, I. J.; Weiss, L. Helv. Chim. Acta 1975, 58, 1535.
24. Dietrich, B.; Lehn, J.-M.; Sauvage, J. P. Tetrahedron Lett. 1969, 2885. Dietrich, B.; Lehn, J.-M.; Sauvage, J. P.; Blanzat, J. Tetrahedron 1973, 29, 1629. Miyazaki, M.; Shimoishi, Y.; Miyata, H.; Tôei, K. J. Inorg. Nucl. Chem. 1974, 36, 2033. Ammann, D.; Bissig, R.; Güggi, M.; Pretsch, E.; Simon, W.; Borowitz, I. J.; Weiss, L. Helv. Chim. Acta 1975, 58, 1535.
25. w = 0.045. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre (CCDC).
26. Galasso, V.; De Alti, G.; Bigotto, A. Tetrahedron 1971, 27, 6151.
27. Le Févre, R. J. W.; Saxby, J. D. J. Chem. Soc. (B) 1966, 1064.
28. 2 = 0.224. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre (CCDC).
29. Czech, A.; Czech, B. P.; Bartsch, R. A. J. Org. Chem. 1988, 53, 5.