Face selectivity in the hydrogenation of calixarene ethers

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9148-9149

  Columbus, Ishay ^a,c   Haj Zaroubi, Manal ^a   Siegel, Jay S ^b   Biali, Silvio E ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c ISRAEL INSTITUTE FOR BIOLOGICAL RESEARCH   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; CYCLOHEXANE; ETHER DERIVATIVE; HYDROGEN;

ARTICLE; CALCULATION; DIASTEREOISOMER; HYDROGENATION; PROTEIN CONFORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032509262     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981551z     Document Type: Article

References (31)

1. For reviews on calixarenes, see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry, Cambridge, 1989. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. (d) Gutsche, C. D. Aldrichim. Acta 1995, 28, 1.
2. For reviews on calixarenes, see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry, Cambridge, 1989. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. (d) Gutsche, C. D. Aldrichim. Acta 1995, 28, 1.
3. For reviews on calixarenes, see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry, Cambridge, 1989. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. (d) Gutsche, C. D. Aldrichim. Acta 1995, 28, 1.
4. For reviews on calixarenes, see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry, Cambridge, 1989. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. (d) Gutsche, C. D. Aldrichim. Acta 1995, 28, 1.
5. For recent studies of cyclophanes incorporating a cyclohexane group, see: (a) Yang, F.-M.; Lin, S.-T. J. Org. Chem. 1997, 62, 2727. (b) Ernst, L.; Hopf, H.; Savinsky, R. Liebig Ann. Recueil 1997, 1915.
6. For recent studies of cyclophanes incorporating a cyclohexane group, see: (a) Yang, F.-M.; Lin, S.-T. J. Org. Chem. 1997, 62, 2727. (b) Ernst, L.; Hopf, H.; Savinsky, R. Liebig Ann. Recueil 1997, 1915.
7. For studies on the hydrogenation of calixarenes, see: (a) Grynszpan, F.; Biali, S. E. Chem. Commun. 1996, 195. (b) Bilyk, A.; Harrowfield, J. M.; Skelton, B. W.; White, A. H. An. Quim. Int. Ed. 1997, 93, 363. (c) Bilyk, A.; Harrowfield, J. M.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1997, 4251. (d) Columbus, I.; Biali, S. E. J. Am. Chem. Soc. 1998, 120, 3060. (e) Columbus, I.; Haj-Zaroubi, M.; Biali, S. E. J. Am. Chem. Soc. in press.
8. For studies on the hydrogenation of calixarenes, see: (a) Grynszpan, F.; Biali, S. E. Chem. Commun. 1996, 195. (b) Bilyk, A.; Harrowfield, J. M.; Skelton, B. W.; White, A. H. An. Quim. Int. Ed. 1997, 93, 363. (c) Bilyk, A.; Harrowfield, J. M.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1997, 4251. (d) Columbus, I.; Biali, S. E. J. Am. Chem. Soc. 1998, 120, 3060. (e) Columbus, I.; Haj-Zaroubi, M.; Biali, S. E. J. Am. Chem. Soc. in press.
9. For studies on the hydrogenation of calixarenes, see: (a) Grynszpan, F.; Biali, S. E. Chem. Commun. 1996, 195. (b) Bilyk, A.; Harrowfield, J. M.; Skelton, B. W.; White, A. H. An. Quim. Int. Ed. 1997, 93, 363. (c) Bilyk, A.; Harrowfield, J. M.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1997, 4251. (d) Columbus, I.; Biali, S. E. J. Am. Chem. Soc. 1998, 120, 3060. (e) Columbus, I.; Haj-Zaroubi, M.; Biali, S. E. J. Am. Chem. Soc. in press.
10. For studies on the hydrogenation of calixarenes, see: (a) Grynszpan, F.; Biali, S. E. Chem. Commun. 1996, 195. (b) Bilyk, A.; Harrowfield, J. M.; Skelton, B. W.; White, A. H. An. Quim. Int. Ed. 1997, 93, 363. (c) Bilyk, A.; Harrowfield, J. M.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1997, 4251. (d) Columbus, I.; Biali, S. E. J. Am. Chem. Soc. 1998, 120, 3060. (e) Columbus, I.; Haj-Zaroubi, M.; Biali, S. E. J. Am. Chem. Soc. in press.
11. For studies on the hydrogenation of calixarenes, see: (a) Grynszpan, F.; Biali, S. E. Chem. Commun. 1996, 195. (b) Bilyk, A.; Harrowfield, J. M.; Skelton, B. W.; White, A. H. An. Quim. Int. Ed. 1997, 93, 363. (c) Bilyk, A.; Harrowfield, J. M.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1997, 4251. (d) Columbus, I.; Biali, S. E. J. Am. Chem. Soc. 1998, 120, 3060. (e) Columbus, I.; Haj-Zaroubi, M.; Biali, S. E. J. Am. Chem. Soc. in press.
12. (a) Verboom, W.; Datta, S.; Asfari, Z.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1992, 57, 5394.
13. (b) Ikeda, A.; Nagasaki, T.; Araki, K.; Shinkai, S. Tetrahedron 1992, 48, 1059.
14. (c) Iwamoto, K.; Araki, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4955.
15. (d) Iki, H.; Kikuchi, T.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1 1993, 205.
16. Hydrogenation of triptycene under kinetic control occurs in an all-syn fashion. See: Farina, M.; Morandi, C.; Mantica, E.; Botta, D. J. Org. Chem. 1977, 42, 2399.
17. 3 complexation of 1 occurs on the exo face. See: Iki, H.; Kikuchi, T.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1 1993, 205.
18. 13C NMR δ 11.11, 15.22, 23.41, 23.73, 28.23, 36.77, 68.72, 80.99 ppm.
19. β located at the exo face in a cis relationship and axial connections of the cyclohexanes to the macrocycle.
20. For recent reviews on the conformation of cyclohexane rings, see: (a) Conformational Behavior of Six Membered Rings; Juaristi, E., Ed.; VCH: New York, 1995. (b) Mann, G. Z. Chem. 1990, 30, 1. (c) Anderson, J. E. In The Chemistry of Alkanes and Cycloalkanes; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1992; Chapter 3. (d) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994.
21. For recent reviews on the conformation of cyclohexane rings, see: (a) Conformational Behavior of Six Membered Rings; Juaristi, E., Ed.; VCH: New York, 1995. (b) Mann, G. Z. Chem. 1990, 30, 1. (c) Anderson, J. E. In The Chemistry of Alkanes and Cycloalkanes; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1992; Chapter 3. (d) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994.
22. For recent reviews on the conformation of cyclohexane rings, see: (a) Conformational Behavior of Six Membered Rings; Juaristi, E., Ed.; VCH: New York, 1995. (b) Mann, G. Z. Chem. 1990, 30, 1. (c) Anderson, J. E. In The Chemistry of Alkanes and Cycloalkanes; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1992; Chapter 3. (d) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994.
23. For recent reviews on the conformation of cyclohexane rings, see: (a) Conformational Behavior of Six Membered Rings; Juaristi, E., Ed.; VCH: New York, 1995. (b) Mann, G. Z. Chem. 1990, 30, 1. (c) Anderson, J. E. In The Chemistry of Alkanes and Cycloalkanes; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1992; Chapter 3. (d) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994.
24. The equatorial disposition of alkyl group in a cyclohexane is favored over the axial one. For exceptions to this rule, see: (a) Golan, O.; Goren, Z.; Biali, S. E. J. Am. Chem. Soc. 1990, 112, 9300. (b) Biali, S. E. J. Org. Chem. 1992, 57, 2979. (c) Kang, F.-A.; Yin, C.-L. J. Am. Chem. Soc. 1997, 119, 8562.
25. The equatorial disposition of alkyl group in a cyclohexane is favored over the axial one. For exceptions to this rule, see: (a) Golan, O.; Goren, Z.; Biali, S. E. J. Am. Chem. Soc. 1990, 112, 9300. (b) Biali, S. E. J. Org. Chem. 1992, 57, 2979. (c) Kang, F.-A.; Yin, C.-L. J. Am. Chem. Soc. 1997, 119, 8562.
26. The equatorial disposition of alkyl group in a cyclohexane is favored over the axial one. For exceptions to this rule, see: (a) Golan, O.; Goren, Z.; Biali, S. E. J. Am. Chem. Soc. 1990, 112, 9300. (b) Biali, S. E. J. Org. Chem. 1992, 57, 2979. (c) Kang, F.-A.; Yin, C.-L. J. Am. Chem. Soc. 1997, 119, 8562.
27. Allinger, N. L. Molecular Mechanics. Operating Instructions for the MM3 Program. 1989 Force Field (updated 5/6/92), Technical Utilization Corp.
28. β identical to 3c-1,3-alt and adopts the equatorial-endo conformation (ref 3e).
29. -1) has been reported for a crowded rotane. See: Fitjer, L.; Steeneck, C.; Gaini-Rahimi, S.; Schröder, U.; Justus, K.; Puder, P.; Dittmer, M.; Hassler, C.; Weiser, J.; Noltemeyer, M.; Teichert, M. J. Am. Chem. Soc. 1998, 120, 317.
30. 1H NMR spectrum, which showed the presence of starting material and propanol.
31. Inspection of models and MM3 calculations indicate that equatorial-exo arrangement of the cyclohexanes in 3a-cone, 3b-partial cone, and 3c-1,3-alt results in severely strained structures.