Rodlike molecules by Kolbe electrolysis

Synthesis

Volumn , Issue 1, 1996, Pages 71-76

  Nuding, G ^a   Vogtle F ^a   Danielmeier, K ^a   Steckhan, E ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Kolbe electrolysis; monoesters of dicarboxylic acids; oligo bicyclo 2.2.2 octane; repetitive synthesis; rodlike molecules

Indexed keywords

ADAMANTANE DERIVATIVE; BICYCLO[2.2.2]OCTANE DERIVATIVE; OLIGOMER;

ARTICLE; DRUG SYNTHESIS; ELECTROCHEMISTRY; TECHNIQUE;

EID: 0030040524     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4152     Document Type: Article

References (56)

1. Stoddart, J. F. Host-Guest Molecular Interactions: From Chemistry to Biology; Ciba Foundation Symposium, Couper, J., Ed.; Chichester; 1991, p 5-22. Lehn, J. M. Angew. Chem. 1990, 102, 1347; Angew. Chem., Int. Ed. Engl. 1990, 29, 1304. Stoddart, J. F. Chem. Aust. 1992, 576.
2. Stoddart, J. F. Host-Guest Molecular Interactions: From Chemistry to Biology; Ciba Foundation Symposium, Couper, J., Ed.; Chichester; 1991, p 5-22. Lehn, J. M. Angew. Chem. 1990, 102, 1347; Angew. Chem., Int. Ed. Engl. 1990, 29, 1304. Stoddart, J. F. Chem. Aust. 1992, 576.
3. Stoddart, J. F. Host-Guest Molecular Interactions: From Chemistry to Biology; Ciba Foundation Symposium, Couper, J., Ed.; Chichester; 1991, p 5-22. Lehn, J. M. Angew. Chem. 1990, 102, 1347; Angew. Chem., Int. Ed. Engl. 1990, 29, 1304. Stoddart, J. F. Chem. Aust. 1992, 576.
4. Stoddart, J. F. Host-Guest Molecular Interactions: From Chemistry to Biology; Ciba Foundation Symposium, Couper, J., Ed.; Chichester; 1991, p 5-22. Lehn, J. M. Angew. Chem. 1990, 102, 1347; Angew. Chem., Int. Ed. Engl. 1990, 29, 1304. Stoddart, J. F. Chem. Aust. 1992, 576.
5. Reiffenrather, V.; Schneider, F. Z. Naturforsch. 1981, 36 A, 1006. Deutscher, H. J.; Seidel, C.; Altmann, H. Z. Chem. 1984, 24, 257.
6. Reiffenrather, V.; Schneider, F. Z. Naturforsch. 1981, 36 A, 1006. Deutscher, H. J.; Seidel, C.; Altmann, H. Z. Chem. 1984, 24, 257.
7. Leyland, B. A.; Jordan, A. D.; Felker, P. K.; Hopfield, J. J.; Zewail, A. H.; Dervan, P. B. J. Phys. Chem. 1985, 89 (26), 5571. De Cola, L.; Balzani, V.; Barigeiletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F.; Nieger, M. Angew. Chem. 1993, 105, 1707; Angew. Chem., Int. Ed. Engl. 1993, 32(11), 1643. De Cola, L.; Balzani, V.; Barigelletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F. Inorg. Chem. 1993, 32(23), 5228. Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933. Gleiter, R.; Barzyk, O. Angew. Chem. 1995, 107, 1094; Angew. Chem., Int. Ed. Engl. 1995, 34, 1001.
8. Leyland, B. A.; Jordan, A. D.; Felker, P. K.; Hopfield, J. J.; Zewail, A. H.; Dervan, P. B. J. Phys. Chem. 1985, 89 (26), 5571. De Cola, L.; Balzani, V.; Barigeiletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F.; Nieger, M. Angew. Chem. 1993, 105, 1707; Angew. Chem., Int. Ed. Engl. 1993, 32(11), 1643. De Cola, L.; Balzani, V.; Barigelletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F. Inorg. Chem. 1993, 32(23), 5228. Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933. Gleiter, R.; Barzyk, O. Angew. Chem. 1995, 107, 1094; Angew. Chem., Int. Ed. Engl. 1995, 34, 1001.
9. Leyland, B. A.; Jordan, A. D.; Felker, P. K.; Hopfield, J. J.; Zewail, A. H.; Dervan, P. B. J. Phys. Chem. 1985, 89 (26), 5571. De Cola, L.; Balzani, V.; Barigeiletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F.; Nieger, M. Angew. Chem. 1993, 105, 1707; Angew. Chem., Int. Ed. Engl. 1993, 32(11), 1643. De Cola, L.; Balzani, V.; Barigelletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F. Inorg. Chem. 1993, 32(23), 5228. Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933. Gleiter, R.; Barzyk, O. Angew. Chem. 1995, 107, 1094; Angew. Chem., Int. Ed. Engl. 1995, 34, 1001.
10. Leyland, B. A.; Jordan, A. D.; Felker, P. K.; Hopfield, J. J.; Zewail, A. H.; Dervan, P. B. J. Phys. Chem. 1985, 89 (26), 5571. De Cola, L.; Balzani, V.; Barigeiletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F.; Nieger, M. Angew. Chem. 1993, 105, 1707; Angew. Chem., Int. Ed. Engl. 1993, 32(11), 1643. De Cola, L.; Balzani, V.; Barigelletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F. Inorg. Chem. 1993, 32(23), 5228. Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933. Gleiter, R.; Barzyk, O. Angew. Chem. 1995, 107, 1094; Angew. Chem., Int. Ed. Engl. 1995, 34, 1001.
11. Leyland, B. A.; Jordan, A. D.; Felker, P. K.; Hopfield, J. J.; Zewail, A. H.; Dervan, P. B. J. Phys. Chem. 1985, 89 (26), 5571. De Cola, L.; Balzani, V.; Barigeiletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F.; Nieger, M. Angew. Chem. 1993, 105, 1707; Angew. Chem., Int. Ed. Engl. 1993, 32(11), 1643. De Cola, L.; Balzani, V.; Barigelletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F. Inorg. Chem. 1993, 32(23), 5228. Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933. Gleiter, R.; Barzyk, O. Angew. Chem. 1995, 107, 1094; Angew. Chem., Int. Ed. Engl. 1995, 34, 1001.
12. Leyland, B. A.; Jordan, A. D.; Felker, P. K.; Hopfield, J. J.; Zewail, A. H.; Dervan, P. B. J. Phys. Chem. 1985, 89 (26), 5571. De Cola, L.; Balzani, V.; Barigeiletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F.; Nieger, M. Angew. Chem. 1993, 105, 1707; Angew. Chem., Int. Ed. Engl. 1993, 32(11), 1643. De Cola, L.; Balzani, V.; Barigelletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F. Inorg. Chem. 1993, 32(23), 5228. Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933. Gleiter, R.; Barzyk, O. Angew. Chem. 1995, 107, 1094; Angew. Chem., Int. Ed. Engl. 1995, 34, 1001.
13. Leyland, B. A.; Jordan, A. D.; Felker, P. K.; Hopfield, J. J.; Zewail, A. H.; Dervan, P. B. J. Phys. Chem. 1985, 89 (26), 5571. De Cola, L.; Balzani, V.; Barigeiletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F.; Nieger, M. Angew. Chem. 1993, 105, 1707; Angew. Chem., Int. Ed. Engl. 1993, 32(11), 1643. De Cola, L.; Balzani, V.; Barigelletti, F.; Flamigni, L.; Belser, P.; von Zelewsky, A.; Frank, M.; Vögtle, F. Inorg. Chem. 1993, 32(23), 5228. Zimmerman, H. E.; Goldman, T. D.; Hirzel, T. K.; Schmidt, S. P. J. Org. Chem. 1980, 45, 3933. Gleiter, R.; Barzyk, O. Angew. Chem. 1995, 107, 1094; Angew. Chem., Int. Ed. Engl. 1995, 34, 1001.
14. Zimmermann, H. E.; King, R. K.; Meinhardt, M. B. J. Org. Chem. 1992, 57, 5484. Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. Hasenrück, K.; Gudipati, S. M.; Lynch, V. M.; Michl, J. J. Org. Chem. 1990, 55, 1013. Moore, J. S. Nature 1993, 361, 119. Ayres, F. D.; Khan, S. I.; Chapman, O. L. Tetrahedron Lett. 1994, 35, 8561. Eaton, P. E.; Tsanaktsidis, J. J. Am. Chem. Soc. 1990, 112, 876. Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553. Kazyushi, N. O.; Mc Murdie, J.; Michl, J. J. Org. Chem. 1991, 56, 307. Van Zorge, J. A.; Strating, J.; Wynberg, H. Recl. Trav. Chim. Pays-Bas 1970, 89, 781.
15. Zimmermann, H. E.; King, R. K.; Meinhardt, M. B. J. Org. Chem. 1992, 57, 5484. Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. Hasenrück, K.; Gudipati, S. M.; Lynch, V. M.; Michl, J. J. Org. Chem. 1990, 55, 1013. Moore, J. S. Nature 1993, 361, 119. Ayres, F. D.; Khan, S. I.; Chapman, O. L. Tetrahedron Lett. 1994, 35, 8561. Eaton, P. E.; Tsanaktsidis, J. J. Am. Chem. Soc. 1990, 112, 876. Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553. Kazyushi, N. O.; Mc Murdie, J.; Michl, J. J. Org. Chem. 1991, 56, 307. Van Zorge, J. A.; Strating, J.; Wynberg, H. Recl. Trav. Chim. Pays-Bas 1970, 89, 781.
16. Zimmermann, H. E.; King, R. K.; Meinhardt, M. B. J. Org. Chem. 1992, 57, 5484. Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. Hasenrück, K.; Gudipati, S. M.; Lynch, V. M.; Michl, J. J. Org. Chem. 1990, 55, 1013. Moore, J. S. Nature 1993, 361, 119. Ayres, F. D.; Khan, S. I.; Chapman, O. L. Tetrahedron Lett. 1994, 35, 8561. Eaton, P. E.; Tsanaktsidis, J. J. Am. Chem. Soc. 1990, 112, 876. Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553. Kazyushi, N. O.; Mc Murdie, J.; Michl, J. J. Org. Chem. 1991, 56, 307. Van Zorge, J. A.; Strating, J.; Wynberg, H. Recl. Trav. Chim. Pays-Bas 1970, 89, 781.
17. Zimmermann, H. E.; King, R. K.; Meinhardt, M. B. J. Org. Chem. 1992, 57, 5484. Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. Hasenrück, K.; Gudipati, S. M.; Lynch, V. M.; Michl, J. J. Org. Chem. 1990, 55, 1013. Moore, J. S. Nature 1993, 361, 119. Ayres, F. D.; Khan, S. I.; Chapman, O. L. Tetrahedron Lett. 1994, 35, 8561. Eaton, P. E.; Tsanaktsidis, J. J. Am. Chem. Soc. 1990, 112, 876. Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553. Kazyushi, N. O.; Mc Murdie, J.; Michl, J. J. Org. Chem. 1991, 56, 307. Van Zorge, J. A.; Strating, J.; Wynberg, H. Recl. Trav. Chim. Pays-Bas 1970, 89, 781.
18. Zimmermann, H. E.; King, R. K.; Meinhardt, M. B. J. Org. Chem. 1992, 57, 5484. Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. Hasenrück, K.; Gudipati, S. M.; Lynch, V. M.; Michl, J. J. Org. Chem. 1990, 55, 1013. Moore, J. S. Nature 1993, 361, 119. Ayres, F. D.; Khan, S. I.; Chapman, O. L. Tetrahedron Lett. 1994, 35, 8561. Eaton, P. E.; Tsanaktsidis, J. J. Am. Chem. Soc. 1990, 112, 876. Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553. Kazyushi, N. O.; Mc Murdie, J.; Michl, J. J. Org. Chem. 1991, 56, 307. Van Zorge, J. A.; Strating, J.; Wynberg, H. Recl. Trav. Chim. Pays-Bas 1970, 89, 781.
19. Zimmermann, H. E.; King, R. K.; Meinhardt, M. B. J. Org. Chem. 1992, 57, 5484. Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. Hasenrück, K.; Gudipati, S. M.; Lynch, V. M.; Michl, J. J. Org. Chem. 1990, 55, 1013. Moore, J. S. Nature 1993, 361, 119. Ayres, F. D.; Khan, S. I.; Chapman, O. L. Tetrahedron Lett. 1994, 35, 8561. Eaton, P. E.; Tsanaktsidis, J. J. Am. Chem. Soc. 1990, 112, 876. Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553. Kazyushi, N. O.; Mc Murdie, J.; Michl, J. J. Org. Chem. 1991, 56, 307. Van Zorge, J. A.; Strating, J.; Wynberg, H. Recl. Trav. Chim. Pays-Bas 1970, 89, 781.
20. Zimmermann, H. E.; King, R. K.; Meinhardt, M. B. J. Org. Chem. 1992, 57, 5484. Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. Hasenrück, K.; Gudipati, S. M.; Lynch, V. M.; Michl, J. J. Org. Chem. 1990, 55, 1013. Moore, J. S. Nature 1993, 361, 119. Ayres, F. D.; Khan, S. I.; Chapman, O. L. Tetrahedron Lett. 1994, 35, 8561. Eaton, P. E.; Tsanaktsidis, J. J. Am. Chem. Soc. 1990, 112, 876. Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553. Kazyushi, N. O.; Mc Murdie, J.; Michl, J. J. Org. Chem. 1991, 56, 307. Van Zorge, J. A.; Strating, J.; Wynberg, H. Recl. Trav. Chim. Pays-Bas 1970, 89, 781.
21. Zimmermann, H. E.; King, R. K.; Meinhardt, M. B. J. Org. Chem. 1992, 57, 5484. Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. Hasenrück, K.; Gudipati, S. M.; Lynch, V. M.; Michl, J. J. Org. Chem. 1990, 55, 1013. Moore, J. S. Nature 1993, 361, 119. Ayres, F. D.; Khan, S. I.; Chapman, O. L. Tetrahedron Lett. 1994, 35, 8561. Eaton, P. E.; Tsanaktsidis, J. J. Am. Chem. Soc. 1990, 112, 876. Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553. Kazyushi, N. O.; Mc Murdie, J.; Michl, J. J. Org. Chem. 1991, 56, 307. Van Zorge, J. A.; Strating, J.; Wynberg, H. Recl. Trav. Chim. Pays-Bas 1970, 89, 781.
22. Zimmermann, H. E.; King, R. K.; Meinhardt, M. B. J. Org. Chem. 1992, 57, 5484. Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601. Hasenrück, K.; Gudipati, S. M.; Lynch, V. M.; Michl, J. J. Org. Chem. 1990, 55, 1013. Moore, J. S. Nature 1993, 361, 119. Ayres, F. D.; Khan, S. I.; Chapman, O. L. Tetrahedron Lett. 1994, 35, 8561. Eaton, P. E.; Tsanaktsidis, J. J. Am. Chem. Soc. 1990, 112, 876. Wiberg, K. B.; Waddell, S. T.; Laidig, K. Tetrahedron Lett. 1986, 27, 1553. Kazyushi, N. O.; Mc Murdie, J.; Michl, J. J. Org. Chem. 1991, 56, 307. Van Zorge, J. A.; Strating, J.; Wynberg, H. Recl. Trav. Chim. Pays-Bas 1970, 89, 781.
23. Vögtle, F.; Buhleier, E.; Wehner, W. Synthesis 1979, 899.
24. Brown, A. C.; Walker, Liebigs Ann. Chem. 1891, 261, 107; Trans. Roy. Soc. Edinburgh, 1891, 36, 291.
25. Brown, A. C.; Walker, Liebigs Ann. Chem. 1891, 261, 107; Trans. Roy. Soc. Edinburgh, 1891, 36, 291.
26. March, J. Advanced Organic Synthesis, third edn.; Wiley p 471. Fichter, F.; Holbro, T. Helv. Chim. Acta 1938, 21, 141.
27. March, J. Advanced Organic Synthesis, third edn.; Wiley p 471. Fichter, F.; Holbro, T. Helv. Chim. Acta 1938, 21, 141.
28. Schäfer, H. J. Top. Curr. Chem. 1990, 152, 91. Weedon, B. L. C. Adv. Org. Chem. 1960, 1, 1. Eberson, L.; Ryde-Petterson, G. Acta Chem. Scand. 1973, 27, 1159. Hawkes, G. E.; Utley, J. H. P; Yates, G. B. J. Chem. Soc., Perkin Trans. 2 1976, 1909. Eberson, L. The Chemistry of Carboxylic Acids and Esters; Patai, S., Ed.; Interscience: London, New York, Sydney, Toronto, 1969, p 53-101.
29. Schäfer, H. J. Top. Curr. Chem. 1990, 152, 91. Weedon, B. L. C. Adv. Org. Chem. 1960, 1, 1. Eberson, L.; Ryde-Petterson, G. Acta Chem. Scand. 1973, 27, 1159. Hawkes, G. E.; Utley, J. H. P; Yates, G. B. J. Chem. Soc., Perkin Trans. 2 1976, 1909. Eberson, L. The Chemistry of Carboxylic Acids and Esters; Patai, S., Ed.; Interscience: London, New York, Sydney, Toronto, 1969, p 53-101.
30. Schäfer, H. J. Top. Curr. Chem. 1990, 152, 91. Weedon, B. L. C. Adv. Org. Chem. 1960, 1, 1. Eberson, L.; Ryde-Petterson, G. Acta Chem. Scand. 1973, 27, 1159. Hawkes, G. E.; Utley, J. H. P; Yates, G. B. J. Chem. Soc., Perkin Trans. 2 1976, 1909. Eberson, L. The Chemistry of Carboxylic Acids and Esters; Patai, S., Ed.; Interscience: London, New York, Sydney, Toronto, 1969, p 53-101.
31. Schäfer, H. J. Top. Curr. Chem. 1990, 152, 91. Weedon, B. L. C. Adv. Org. Chem. 1960, 1, 1. Eberson, L.; Ryde-Petterson, G. Acta Chem. Scand. 1973, 27, 1159. Hawkes, G. E.; Utley, J. H. P; Yates, G. B. J. Chem. Soc., Perkin Trans. 2 1976, 1909. Eberson, L. The Chemistry of Carboxylic Acids and Esters; Patai, S., Ed.; Interscience: London, New York, Sydney, Toronto, 1969, p 53-101.
32. Schäfer, H. J. Top. Curr. Chem. 1990, 152, 91. Weedon, B. L. C. Adv. Org. Chem. 1960, 1, 1. Eberson, L.; Ryde-Petterson, G. Acta Chem. Scand. 1973, 27, 1159. Hawkes, G. E.; Utley, J. H. P; Yates, G. B. J. Chem. Soc., Perkin Trans. 2 1976, 1909. Eberson, L. The Chemistry of Carboxylic Acids and Esters; Patai, S., Ed.; Interscience: London, New York, Sydney, Toronto, 1969, p 53-101.
33. Woolford, R. G. Can. J. Chem. 1962, 40, 1846; 1964, 1788.
34. Woolford, R. G. Can. J. Chem. 1962, 40, 1846; 1964, 1788.
35. Ph. D. thesis, Frank, M., Universität Bonn, Germany, 1993.
36. Electrolysis of bicyclo[1.1.1]pentane-3,3′-dicarboxylic acid was described by: Kazynski, P.; Mc Murdie, N. O.; Michl, J. J. Org. Chem. 1991, 56, 307. Electrolysis of apocamphane-1-carboxylic acid by. Muhs, M. A. Ph. D. Thesis, University of Washington, Seattle, USA 1954.
37. Electrolysis of bicyclo[1.1.1]pentane-3,3′-dicarboxylic acid was described by: Kazynski, P.; Mc Murdie, N. O.; Michl, J. J. Org. Chem. 1991, 56, 307. Electrolysis of apocamphane-1-carboxylic acid by. Muhs, M. A. Ph. D. Thesis, University of Washington, Seattle, USA 1954.
38. Hofer, H.; Moest, M. Liebigs Ann. Chem. 1902, 323, 285.
39. Other synthetic routes to 1,1′-biadamantane: Reinhardt, H. F. J. Org. Chem. 1962, 27, 3258.
40. Identification by NMR spectra was ambiguous.
41. Gleiter, R.; Schäfer, W. Acc. Chem. Res. 1990, 23, 369.
42. Holtz, H. D.; Stock, L. M. J. Am. Chem. Soc. 1964, 5183.
43. Bagal, M. L.; Lantovoev, V. I. Zh. Org. Khim. 1973, 9(2), 291.
44. We thank C. Steinbeck and G. Harder for performing the NMR spectra and Prof. E. Breitmaier for advice concerning the interpretation of the NMR spectra.
45. We thank Dr. G. Eckhardt and Dr. D. Karbach for their efforts to detect the higher "rods".
46. Della, E. W.; Tsanaktsidis, J. Aust. J. Chem. 1985, 38, 1705.
47. Roberts, J. D.; Moreland, W. T.; Frazer, W. J. Am. Chem. Soc. 1963, 75, 637. Another synthesis of the semi-ester is described by: Holtz, H. D.; Stock, L. M. J. Am. Chem. Soc. 1964, 86, 5183.
48. Roberts, J. D.; Moreland, W. T.; Frazer, W. J. Am. Chem. Soc. 1963, 75, 637. Another synthesis of the semi-ester is described by: Holtz, H. D.; Stock, L. M. J. Am. Chem. Soc. 1964, 86, 5183.
49. Adcock, W.; Abeywickrema, A. N. J. Org. Chem. 1982, 15, 2950.
50. Mozingo, R. Organic Synthesis, Coll. Vol. III; Wiley: New York, 1955, p 183.
51. Landa, S.; Kamyzek, Z. Coll. Czech. Chem. Commun. 1959, 24, 1325. Landa, S.; Kamyzek, Z. Coll. Czech. Chem. Commun. 1959, 24, 4004.
52. Landa, S.; Kamyzek, Z. Coll. Czech. Chem. Commun. 1959, 24, 1325. Landa, S.; Kamyzek, Z. Coll. Czech. Chem. Commun. 1959, 24, 4004.
53. Luh, T.-Y; Stock, L. M. J. Org. Chem. 1977, 16, 2791. Eaton, P. E.; Cole, T. W., Jr. J. Am. Chem. Soc. 1964, 86, 3157.
54. Luh, T.-Y; Stock, L. M. J. Org. Chem. 1977, 16, 2791. Eaton, P. E.; Cole, T. W., Jr. J. Am. Chem. Soc. 1964, 86, 3157.
55. Klotz-Berendes, B.; Schäfer, H. J.; Grehl, M.; Fröhlich, R. Angew. Chem. 1995, 107, 218; Angew. Chem., Int. Ed. Engl. 1995, 34, 189.
56. Klotz-Berendes, B.; Schäfer, H. J.; Grehl, M.; Fröhlich, R. Angew. Chem. 1995, 107, 218; Angew. Chem., Int. Ed. Engl. 1995, 34, 189.