Selective upper rim functionalization and lower rim bridge building with calix[4]arenes and calix[6]arenes

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2511-2516

  Kanamathareddy, Suseela ^a   Gutsche, C David ^a  

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000767034     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952054a     Document Type: Article

References (24)

1. Paper 44 in the series Calixarenes. For paper 43, cf. Gibbs, C. G.; Sujeeth; P. K.; Rogers, J. S.; Stanley, G. G., Krawiec, M.; Watson, W. H.; Gutsche, C. D. J. Org. Chem. 1995, 60, 8394.
2. (a) Gutsche, C. D. Calixarenes. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: London, 1989.
3. (b) Calixarenes, A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991.
4. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
5. (d) Gutsche, C. D. Aldrichimica Acta 1995, 28, 3-9.
6. Kanamathareddy, S.; Gutsche, C. D. J. Org. Chem. 1992, 57, 3160.
7. de Mendoza, J.; Carramolino, M.; Cuevas, F.; Nieto, P. D.; Prados, P.; Reinhoudt, D. N. Verboom, W.; Ungaro, R.; Casnati, A. Synthesis 1994, 47.
8. Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032.
9. Gutsche, C. D.; Nam, K C. J. Am. Chem. Soc. 1988, 110, 6153.
10. Compound 21 has been described with brief experimental detail (Miura, M.; Gabel, D.; Oenbrink, G.; Fairchild, R. G. Tetrahedron Lett. 1990, 31, 2247). Compound 22 has been reported in the patent literature [Karrer, F.; Farooq, S.; Drabek, J.; Meyer, W.; Gsell, L. Ger. Offen. 2,654,293 (Chem. Abstr. 1977, 87, 84693k); Sumitomo Chemical Co., Ltd. Fr 2,043,019 (Chem. Abstr. 1972, 76, 3557s)]. Compound 23 has been reported in the patent literature [Henrick, C. A.; Garcia, B. A. Ger. Offen. 2,812,169 (Chem. Abstr. 1979, 90, 122072d); US 4,243,-819 (Chem. Abstr. 1982, 96, 123297s)] 2,5-Bis(propargyloxy)benzoic esters have been reported by Brown, A. B.; Whitlock, H. W., Jr. Synth. Commun. 1993, 23, 23.
11. Compound 21 has been described with brief experimental detail (Miura, M.; Gabel, D.; Oenbrink, G.; Fairchild, R. G. Tetrahedron Lett. 1990, 31, 2247). Compound 22 has been reported in the patent literature [Karrer, F.; Farooq, S.; Drabek, J.; Meyer, W.; Gsell, L. Ger. Offen. 2,654,293 (Chem. Abstr. 1977, 87, 84693k); Sumitomo Chemical Co., Ltd. Fr 2,043,019 (Chem. Abstr. 1972, 76, 3557s)]. Compound 23 has been reported in the patent literature [Henrick, C. A.; Garcia, B. A. Ger. Offen. 2,812,169 (Chem. Abstr. 1979, 90, 122072d); US 4,243,-819 (Chem. Abstr. 1982, 96, 123297s)] 2,5-Bis(propargyloxy)benzoic esters have been reported by Brown, A. B.; Whitlock, H. W., Jr. Synth. Commun. 1993, 23, 23.
12. Compound 21 has been described with brief experimental detail (Miura, M.; Gabel, D.; Oenbrink, G.; Fairchild, R. G. Tetrahedron Lett. 1990, 31, 2247). Compound 22 has been reported in the patent literature [Karrer, F.; Farooq, S.; Drabek, J.; Meyer, W.; Gsell, L. Ger. Offen. 2,654,293 (Chem. Abstr. 1977, 87, 84693k); Sumitomo Chemical Co., Ltd. Fr 2,043,019 (Chem. Abstr. 1972, 76, 3557s)]. Compound 23 has been reported in the patent literature [Henrick, C. A.; Garcia, B. A. Ger. Offen. 2,812,169 (Chem. Abstr. 1979, 90, 122072d); US 4,243,-819 (Chem. Abstr. 1982, 96, 123297s)] 2,5-Bis(propargyloxy)benzoic esters have been reported by Brown, A. B.; Whitlock, H. W., Jr. Synth. Commun. 1993, 23, 23.
13. Compound 21 has been described with brief experimental detail (Miura, M.; Gabel, D.; Oenbrink, G.; Fairchild, R. G. Tetrahedron Lett. 1990, 31, 2247). Compound 22 has been reported in the patent literature [Karrer, F.; Farooq, S.; Drabek, J.; Meyer, W.; Gsell, L. Ger. Offen. 2,654,293 (Chem. Abstr. 1977, 87, 84693k); Sumitomo Chemical Co., Ltd. Fr 2,043,019 (Chem. Abstr. 1972, 76, 3557s)]. Compound 23 has been reported in the patent literature [Henrick, C. A.; Garcia, B. A. Ger. Offen. 2,812,169 (Chem. Abstr. 1979, 90, 122072d); US 4,243,-819 (Chem. Abstr. 1982, 96, 123297s)] 2,5-Bis(propargyloxy)benzoic esters have been reported by Brown, A. B.; Whitlock, H. W., Jr. Synth. Commun. 1993, 23, 23.
14. Compound 21 has been described with brief experimental detail (Miura, M.; Gabel, D.; Oenbrink, G.; Fairchild, R. G. Tetrahedron Lett. 1990, 31, 2247). Compound 22 has been reported in the patent literature [Karrer, F.; Farooq, S.; Drabek, J.; Meyer, W.; Gsell, L. Ger. Offen. 2,654,293 (Chem. Abstr. 1977, 87, 84693k); Sumitomo Chemical Co., Ltd. Fr 2,043,019 (Chem. Abstr. 1972, 76, 3557s)]. Compound 23 has been reported in the patent literature [Henrick, C. A.; Garcia, B. A. Ger. Offen. 2,812,169 (Chem. Abstr. 1979, 90, 122072d); US 4,243,-819 (Chem. Abstr. 1982, 96, 123297s)] 2,5-Bis(propargyloxy)benzoic esters have been reported by Brown, A. B.; Whitlock, H. W., Jr. Synth. Commun. 1993, 23, 23.
15. Compound 21 has been described with brief experimental detail (Miura, M.; Gabel, D.; Oenbrink, G.; Fairchild, R. G. Tetrahedron Lett. 1990, 31, 2247). Compound 22 has been reported in the patent literature [Karrer, F.; Farooq, S.; Drabek, J.; Meyer, W.; Gsell, L. Ger. Offen. 2,654,293 (Chem. Abstr. 1977, 87, 84693k); Sumitomo Chemical Co., Ltd. Fr 2,043,019 (Chem. Abstr. 1972, 76, 3557s)]. Compound 23 has been reported in the patent literature [Henrick, C. A.; Garcia, B. A. Ger. Offen. 2,812,169 (Chem. Abstr. 1979, 90, 122072d); US 4,243,-819 (Chem. Abstr. 1982, 96, 123297s)] 2,5-Bis(propargyloxy)benzoic esters have been reported by Brown, A. B.; Whitlock, H. W., Jr. Synth. Commun. 1993, 23, 23.
16. Dijkstra, P. J.; Brunink, J. A. J.; Bugge, K. E.; Reinhoudt, D. N.; Harkema, S., Ungaro, Ugozzoli, Ghidini, E. J. Am. Chem. Soc 1989, 111, 7567. Gutsche, C. D.; Reddy, P. A. J. Org. Chem. 1991, 56, 4783.
17. Dijkstra, P. J.; Brunink, J. A. J.; Bugge, K. E.; Reinhoudt, D. N.; Harkema, S., Ungaro, Ugozzoli, Ghidini, E. J. Am. Chem. Soc 1989, 111, 7567. Gutsche, C. D.; Reddy, P. A. J. Org. Chem. 1991, 56, 4783.
18. Casnati, A.; Minari, P.; Pochini, A.; Ungaro, R. J. Chem. Soc. Chem.Commun. 1991, 1413. Kanamathareddy, S.; Gutsche, C. D. J. Am. Chem. Soc. 1993, 115, 6572.
19. Casnati, A.; Minari, P.; Pochini, A.; Ungaro, R. J. Chem. Soc. Chem.Commun. 1991, 1413. Kanamathareddy, S.; Gutsche, C. D. J. Am. Chem. Soc. 1993, 115, 6572.
20. Gutsche, C. D.; See. K. A. J. Org. Chem. 1992, 57, 4527.
21. For details of nomenclature, cf. Kanamathareddy, S.; Gutsche, C. D. J. Am. Chem. Soc. 1993, 115, 6572.
22. 13C NMR were recorded at 300 and 75 MHz, respectively. TLC analyses were carried out on Analtech silica gel plates (absorbent thickness 250 μm) containing a fluorescent indicator. TLC analyses were carried out on Analtech silica gel plates (absorbant thickness 250 μm) containing a fluorescent indicator. Chromatography was carried out with J. T. Baker silica gel JT7042-2 (40 μm particles) on columns 50 mm in diameter filled to a height of ca. 7 in. Elution rates were 2 in./min; fractions of 50 mL were collected. Analytical samples were dried at least 36 h at 100-140°C and 1-2 mm of pressure.
23. We are indebted to Wenfang Miao, Department of Chemistry, Texas Christian University, for providing this mass spectrum.
24. Mass sectrum provided by the Washington University Mass Spectrometry Resource, an NIH Research Resource (Grant P41RR0954).