Synthesis of bridged and oligocalix[4]arenes via ruthenium-catalysed ring closing metathesis

Chemical Communications

Volumn , Issue 14, 1996, Pages 1689-1690

  McKervey, M Anthony ^a   Pitarch, Miguel ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000112278     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960001689     Document Type: Article

References (18)

1. G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1992, 114, 5426; G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 7324; G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1993, 115, 3800; G. C. Fu, S. T. Nguyen and R. H. Grubbs, J. Am. Chem. Soc., 1993, 115, 9856; S. J. Miller, S. H. Kim, Z. R. Chen and R. H. Grubbs, J. Am. Chem. Soc., 1995, 117, 2108.
2. G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1992, 114, 5426; G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 7324; G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1993, 115, 3800; G. C. Fu, S. T. Nguyen and R. H. Grubbs, J. Am. Chem. Soc., 1993, 115, 9856; S. J. Miller, S. H. Kim, Z. R. Chen and R. H. Grubbs, J. Am. Chem. Soc., 1995, 117, 2108.
3. G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1992, 114, 5426; G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 7324; G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1993, 115, 3800; G. C. Fu, S. T. Nguyen and R. H. Grubbs, J. Am. Chem. Soc., 1993, 115, 9856; S. J. Miller, S. H. Kim, Z. R. Chen and R. H. Grubbs, J. Am. Chem. Soc., 1995, 117, 2108.
4. G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1992, 114, 5426; G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 7324; G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1993, 115, 3800; G. C. Fu, S. T. Nguyen and R. H. Grubbs, J. Am. Chem. Soc., 1993, 115, 9856; S. J. Miller, S. H. Kim, Z. R. Chen and R. H. Grubbs, J. Am. Chem. Soc., 1995, 117, 2108.
5. G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1992, 114, 5426; G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc. 1992, 114, 7324; G. C. Fu and R. H. Grubbs, J. Am. Chem. Soc., 1993, 115, 3800; G. C. Fu, S. T. Nguyen and R. H. Grubbs, J. Am. Chem. Soc., 1993, 115, 9856; S. J. Miller, S. H. Kim, Z. R. Chen and R. H. Grubbs, J. Am. Chem. Soc., 1995, 117, 2108.
6. A. F. Houri, Z. Xu, D. A. Cogan and A. H. Hoveyda, J. Am. Chem. Soc., 1995, 117, 2943.
7. S. Kanamathareddy and C. D. Gutsche, J.Org. Chem., 1995, 60, 6070; P. Lhotak and S. Shinkai, Tetrahedron Lett., 1996, 37, 645. Other examples of bridged calixarenes and double calixarenes have been reported by: H. Goldmann, W. Vogt, E. Paulus and V. Böhmer, Tetrahedron Lett., 1988, 110, 6811; J.-D. van Loon, L. D. Groenen, S. S. Wijmenga, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2378; J. Blixt and C. Detellier, J. Am. Chem. Soc., 1992, 116, 11 957; A. Arduini, G. Manfredi, A. Pochini, A. R. Sicuri and R. Ungaro, J. Chem. Soc. Chem. Commun., 1991, 936; A. Ikeda and S. Shinkai, J. Chem. Soc. Perkin Trans. I, 1993, 2671; D. N. Reinhoudt, P. J. Dijkstra, P. J. A. in't Veld, K. E. Bugge, S. Harkema, R. Ungaro and E. Ghidini, J. Am. Chem. Soc., 1987, 109, 4761. For a review of the synthesis of double calix[4]arene, see: Z. Asfari, J. Weiss and J. Vicens, Synlett, 1993, 719 and additional references can also be obtained from Z. Asfari, S. Wenger and J. Vicens, J. Incl. Phenom., 1994, 19, 137. For other more general examples of calix bridges, see: V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
8. S. Kanamathareddy and C. D. Gutsche, J.Org. Chem., 1995, 60, 6070; P. Lhotak and S. Shinkai, Tetrahedron Lett., 1996, 37, 645. Other examples of bridged calixarenes and double calixarenes have been reported by: H. Goldmann, W. Vogt, E. Paulus and V. Böhmer, Tetrahedron Lett., 1988, 110, 6811; J.-D. van Loon, L. D. Groenen, S. S. Wijmenga, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2378; J. Blixt and C. Detellier, J. Am. Chem. Soc., 1992, 116, 11 957; A. Arduini, G. Manfredi, A. Pochini, A. R. Sicuri and R. Ungaro, J. Chem. Soc. Chem. Commun., 1991, 936; A. Ikeda and S. Shinkai, J. Chem. Soc. Perkin Trans. I, 1993, 2671; D. N. Reinhoudt, P. J. Dijkstra, P. J. A. in't Veld, K. E. Bugge, S. Harkema, R. Ungaro and E. Ghidini, J. Am. Chem. Soc., 1987, 109, 4761. For a review of the synthesis of double calix[4]arene, see: Z. Asfari, J. Weiss and J. Vicens, Synlett, 1993, 719 and additional references can also be obtained from Z. Asfari, S. Wenger and J. Vicens, J. Incl. Phenom., 1994, 19, 137. For other more general examples of calix bridges, see: V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
9. S. Kanamathareddy and C. D. Gutsche, J.Org. Chem., 1995, 60, 6070; P. Lhotak and S. Shinkai, Tetrahedron Lett., 1996, 37, 645. Other examples of bridged calixarenes and double calixarenes have been reported by: H. Goldmann, W. Vogt, E. Paulus and V. Böhmer, Tetrahedron Lett., 1988, 110, 6811; J.-D. van Loon, L. D. Groenen, S. S. Wijmenga, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2378; J. Blixt and C. Detellier, J. Am. Chem. Soc., 1992, 116, 11 957; A. Arduini, G. Manfredi, A. Pochini, A. R. Sicuri and R. Ungaro, J. Chem. Soc. Chem. Commun., 1991, 936; A. Ikeda and S. Shinkai, J. Chem. Soc. Perkin Trans. I, 1993, 2671; D. N. Reinhoudt, P. J. Dijkstra, P. J. A. in't Veld, K. E. Bugge, S. Harkema, R. Ungaro and E. Ghidini, J. Am. Chem. Soc., 1987, 109, 4761. For a review of the synthesis of double calix[4]arene, see: Z. Asfari, J. Weiss and J. Vicens, Synlett, 1993, 719 and additional references can also be obtained from Z. Asfari, S. Wenger and J. Vicens, J. Incl. Phenom., 1994, 19, 137. For other more general examples of calix bridges, see: V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
10. S. Kanamathareddy and C. D. Gutsche, J.Org. Chem., 1995, 60, 6070; P. Lhotak and S. Shinkai, Tetrahedron Lett., 1996, 37, 645. Other examples of bridged calixarenes and double calixarenes have been reported by: H. Goldmann, W. Vogt, E. Paulus and V. Böhmer, Tetrahedron Lett., 1988, 110, 6811; J.-D. van Loon, L. D. Groenen, S. S. Wijmenga, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2378; J. Blixt and C. Detellier, J. Am. Chem. Soc., 1992, 116, 11 957; A. Arduini, G. Manfredi, A. Pochini, A. R. Sicuri and R. Ungaro, J. Chem. Soc. Chem. Commun., 1991, 936; A. Ikeda and S. Shinkai, J. Chem. Soc. Perkin Trans. I, 1993, 2671; D. N. Reinhoudt, P. J. Dijkstra, P. J. A. in't Veld, K. E. Bugge, S. Harkema, R. Ungaro and E. Ghidini, J. Am. Chem. Soc., 1987, 109, 4761. For a review of the synthesis of double calix[4]arene, see: Z. Asfari, J. Weiss and J. Vicens, Synlett, 1993, 719 and additional references can also be obtained from Z. Asfari, S. Wenger and J. Vicens, J. Incl. Phenom., 1994, 19, 137. For other more general examples of calix bridges, see: V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
11. S. Kanamathareddy and C. D. Gutsche, J.Org. Chem., 1995, 60, 6070; P. Lhotak and S. Shinkai, Tetrahedron Lett., 1996, 37, 645. Other examples of bridged calixarenes and double calixarenes have been reported by: H. Goldmann, W. Vogt, E. Paulus and V. Böhmer, Tetrahedron Lett., 1988, 110, 6811; J.-D. van Loon, L. D. Groenen, S. S. Wijmenga, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2378; J. Blixt and C. Detellier, J. Am. Chem. Soc., 1992, 116, 11 957; A. Arduini, G. Manfredi, A. Pochini, A. R. Sicuri and R. Ungaro, J. Chem. Soc. Chem. Commun., 1991, 936; A. Ikeda and S. Shinkai, J. Chem. Soc. Perkin Trans. I, 1993, 2671; D. N. Reinhoudt, P. J. Dijkstra, P. J. A. in't Veld, K. E. Bugge, S. Harkema, R. Ungaro and E. Ghidini, J. Am. Chem. Soc., 1987, 109, 4761. For a review of the synthesis of double calix[4]arene, see: Z. Asfari, J. Weiss and J. Vicens, Synlett, 1993, 719 and additional references can also be obtained from Z. Asfari, S. Wenger and J. Vicens, J. Incl. Phenom., 1994, 19, 137. For other more general examples of calix bridges, see: V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
12. S. Kanamathareddy and C. D. Gutsche, J.Org. Chem., 1995, 60, 6070; P. Lhotak and S. Shinkai, Tetrahedron Lett., 1996, 37, 645. Other examples of bridged calixarenes and double calixarenes have been reported by: H. Goldmann, W. Vogt, E. Paulus and V. Böhmer, Tetrahedron Lett., 1988, 110, 6811; J.-D. van Loon, L. D. Groenen, S. S. Wijmenga, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2378; J. Blixt and C. Detellier, J. Am. Chem. Soc., 1992, 116, 11 957; A. Arduini, G. Manfredi, A. Pochini, A. R. Sicuri and R. Ungaro, J. Chem. Soc. Chem. Commun., 1991, 936; A. Ikeda and S. Shinkai, J. Chem. Soc. Perkin Trans. I, 1993, 2671; D. N. Reinhoudt, P. J. Dijkstra, P. J. A. in't Veld, K. E. Bugge, S. Harkema, R. Ungaro and E. Ghidini, J. Am. Chem. Soc., 1987, 109, 4761. For a review of the synthesis of double calix[4]arene, see: Z. Asfari, J. Weiss and J. Vicens, Synlett, 1993, 719 and additional references can also be obtained from Z. Asfari, S. Wenger and J. Vicens, J. Incl. Phenom., 1994, 19, 137. For other more general examples of calix bridges, see: V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
13. S. Kanamathareddy and C. D. Gutsche, J.Org. Chem., 1995, 60, 6070; P. Lhotak and S. Shinkai, Tetrahedron Lett., 1996, 37, 645. Other examples of bridged calixarenes and double calixarenes have been reported by: H. Goldmann, W. Vogt, E. Paulus and V. Böhmer, Tetrahedron Lett., 1988, 110, 6811; J.-D. van Loon, L. D. Groenen, S. S. Wijmenga, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2378; J. Blixt and C. Detellier, J. Am. Chem. Soc., 1992, 116, 11 957; A. Arduini, G. Manfredi, A. Pochini, A. R. Sicuri and R. Ungaro, J. Chem. Soc. Chem. Commun., 1991, 936; A. Ikeda and S. Shinkai, J. Chem. Soc. Perkin Trans. I, 1993, 2671; D. N. Reinhoudt, P. J. Dijkstra, P. J. A. in't Veld, K. E. Bugge, S. Harkema, R. Ungaro and E. Ghidini, J. Am. Chem. Soc., 1987, 109, 4761. For a review of the synthesis of double calix[4]arene, see: Z. Asfari, J. Weiss and J. Vicens, Synlett, 1993, 719 and additional references can also be obtained from Z. Asfari, S. Wenger and J. Vicens, J. Incl. Phenom., 1994, 19, 137. For other more general examples of calix bridges, see: V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
14. S. Kanamathareddy and C. D. Gutsche, J.Org. Chem., 1995, 60, 6070; P. Lhotak and S. Shinkai, Tetrahedron Lett., 1996, 37, 645. Other examples of bridged calixarenes and double calixarenes have been reported by: H. Goldmann, W. Vogt, E. Paulus and V. Böhmer, Tetrahedron Lett., 1988, 110, 6811; J.-D. van Loon, L. D. Groenen, S. S. Wijmenga, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2378; J. Blixt and C. Detellier, J. Am. Chem. Soc., 1992, 116, 11 957; A. Arduini, G. Manfredi, A. Pochini, A. R. Sicuri and R. Ungaro, J. Chem. Soc. Chem. Commun., 1991, 936; A. Ikeda and S. Shinkai, J. Chem. Soc. Perkin Trans. I, 1993, 2671; D. N. Reinhoudt, P. J. Dijkstra, P. J. A. in't Veld, K. E. Bugge, S. Harkema, R. Ungaro and E. Ghidini, J. Am. Chem. Soc., 1987, 109, 4761. For a review of the synthesis of double calix[4]arene, see: Z. Asfari, J. Weiss and J. Vicens, Synlett, 1993, 719 and additional references can also be obtained from Z. Asfari, S. Wenger and J. Vicens, J. Incl. Phenom., 1994, 19, 137. For other more general examples of calix bridges, see: V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
15. S. Kanamathareddy and C. D. Gutsche, J.Org. Chem., 1995, 60, 6070; P. Lhotak and S. Shinkai, Tetrahedron Lett., 1996, 37, 645. Other examples of bridged calixarenes and double calixarenes have been reported by: H. Goldmann, W. Vogt, E. Paulus and V. Böhmer, Tetrahedron Lett., 1988, 110, 6811; J.-D. van Loon, L. D. Groenen, S. S. Wijmenga, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2378; J. Blixt and C. Detellier, J. Am. Chem. Soc., 1992, 116, 11 957; A. Arduini, G. Manfredi, A. Pochini, A. R. Sicuri and R. Ungaro, J. Chem. Soc. Chem. Commun., 1991, 936; A. Ikeda and S. Shinkai, J. Chem. Soc. Perkin Trans. I, 1993, 2671; D. N. Reinhoudt, P. J. Dijkstra, P. J. A. in't Veld, K. E. Bugge, S. Harkema, R. Ungaro and E. Ghidini, J. Am. Chem. Soc., 1987, 109, 4761. For a review of the synthesis of double calix[4]arene, see: Z. Asfari, J. Weiss and J. Vicens, Synlett, 1993, 719 and additional references can also be obtained from Z. Asfari, S. Wenger and J. Vicens, J. Incl. Phenom., 1994, 19, 137. For other more general examples of calix bridges, see: V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
16. S. Kanamathareddy and C. D. Gutsche, J.Org. Chem., 1995, 60, 6070; P. Lhotak and S. Shinkai, Tetrahedron Lett., 1996, 37, 645. Other examples of bridged calixarenes and double calixarenes have been reported by: H. Goldmann, W. Vogt, E. Paulus and V. Böhmer, Tetrahedron Lett., 1988, 110, 6811; J.-D. van Loon, L. D. Groenen, S. S. Wijmenga, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2378; J. Blixt and C. Detellier, J. Am. Chem. Soc., 1992, 116, 11 957; A. Arduini, G. Manfredi, A. Pochini, A. R. Sicuri and R. Ungaro, J. Chem. Soc. Chem. Commun., 1991, 936; A. Ikeda and S. Shinkai, J. Chem. Soc. Perkin Trans. I, 1993, 2671; D. N. Reinhoudt, P. J. Dijkstra, P. J. A. in't Veld, K. E. Bugge, S. Harkema, R. Ungaro and E. Ghidini, J. Am. Chem. Soc., 1987, 109, 4761. For a review of the synthesis of double calix[4]arene, see: Z. Asfari, J. Weiss and J. Vicens, Synlett, 1993, 719 and additional references can also be obtained from Z. Asfari, S. Wenger and J. Vicens, J. Incl. Phenom., 1994, 19, 137. For other more general examples of calix bridges, see: V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
17. S. Kanamathareddy and C. D. Gutsche, J.Org. Chem., 1995, 60, 6070; P. Lhotak and S. Shinkai, Tetrahedron Lett., 1996, 37, 645. Other examples of bridged calixarenes and double calixarenes have been reported by: H. Goldmann, W. Vogt, E. Paulus and V. Böhmer, Tetrahedron Lett., 1988, 110, 6811; J.-D. van Loon, L. D. Groenen, S. S. Wijmenga, W. Verboom and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2378; J. Blixt and C. Detellier, J. Am. Chem. Soc., 1992, 116, 11 957; A. Arduini, G. Manfredi, A. Pochini, A. R. Sicuri and R. Ungaro, J. Chem. Soc. Chem. Commun., 1991, 936; A. Ikeda and S. Shinkai, J. Chem. Soc. Perkin Trans. I, 1993, 2671; D. N. Reinhoudt, P. J. Dijkstra, P. J. A. in't Veld, K. E. Bugge, S. Harkema, R. Ungaro and E. Ghidini, J. Am. Chem. Soc., 1987, 109, 4761. For a review of the synthesis of double calix[4]arene, see: Z. Asfari, J. Weiss and J. Vicens, Synlett, 1993, 719 and additional references can also be obtained from Z. Asfari, S. Wenger and J. Vicens, J. Incl. Phenom., 1994, 19, 137. For other more general examples of calix bridges, see: V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
18. P. Schawb, M. B. France, J. W. Ziller and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 1995, 34(18), 2039.