The syntheses of pyrazino-containing sultines and their application in Diels-Alder reactions with electron-poor olefins and [60]fullerene

Journal of Organic Chemistry

Volumn 65, Issue 11, 2000, Pages 3395-3403

  Liu, Jing Horng ^a   Wu, An Tai ^a   Huang, Ming Hwei ^a   Wu, Chein Wei ^a   Chung, Wen Sheng ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; FULLERENE DERIVATIVE; PYRAZINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0034595627     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9918448     Document Type: Article

References (65)

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17. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry, see: (a) Oppolzer, W. Synthesis 1978, 793; Heterocycles 1980, 14, 1615. (b) Kametani, T. Pure Appl. Chem. 1979, 51, 747. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (d) Martín, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237. (e) Chou, T.-S. Rev. Heteroat. Chem. 1993, 8, 65. (f) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (g) Collier, S. J.; Storr, R. C. Prog. Heterocycl.c Chem. 1998, 10, 25. (h) Segura, J. L.; Martín, N. Chem. Rev. 1999, 99, 3199.
18. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry, see: (a) Oppolzer, W. Synthesis 1978, 793; Heterocycles 1980, 14, 1615. (b) Kametani, T. Pure Appl. Chem. 1979, 51, 747. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (d) Martín, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237. (e) Chou, T.-S. Rev. Heteroat. Chem. 1993, 8, 65. (f) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (g) Collier, S. J.; Storr, R. C. Prog. Heterocycl.c Chem. 1998, 10, 25. (h) Segura, J. L.; Martín, N. Chem. Rev. 1999, 99, 3199.
19. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry, see: (a) Oppolzer, W. Synthesis 1978, 793; Heterocycles 1980, 14, 1615. (b) Kametani, T. Pure Appl. Chem. 1979, 51, 747. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (d) Martín, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237. (e) Chou, T.-S. Rev. Heteroat. Chem. 1993, 8, 65. (f) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (g) Collier, S. J.; Storr, R. C. Prog. Heterocycl.c Chem. 1998, 10, 25. (h) Segura, J. L.; Martín, N. Chem. Rev. 1999, 99, 3199.
20. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry, see: (a) Oppolzer, W. Synthesis 1978, 793; Heterocycles 1980, 14, 1615. (b) Kametani, T. Pure Appl. Chem. 1979, 51, 747. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (d) Martín, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237. (e) Chou, T.-S. Rev. Heteroat. Chem. 1993, 8, 65. (f) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (g) Collier, S. J.; Storr, R. C. Prog. Heterocycl.c Chem. 1998, 10, 25. (h) Segura, J. L.; Martín, N. Chem. Rev. 1999, 99, 3199.
21. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry, see: (a) Oppolzer, W. Synthesis 1978, 793; Heterocycles 1980, 14, 1615. (b) Kametani, T. Pure Appl. Chem. 1979, 51, 747. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (d) Martín, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237. (e) Chou, T.-S. Rev. Heteroat. Chem. 1993, 8, 65. (f) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (g) Collier, S. J.; Storr, R. C. Prog. Heterocycl.c Chem. 1998, 10, 25. (h) Segura, J. L.; Martín, N. Chem. Rev. 1999, 99, 3199.
22. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry, see: (a) Oppolzer, W. Synthesis 1978, 793; Heterocycles 1980, 14, 1615. (b) Kametani, T. Pure Appl. Chem. 1979, 51, 747. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (d) Martín, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237. (e) Chou, T.-S. Rev. Heteroat. Chem. 1993, 8, 65. (f) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (g) Collier, S. J.; Storr, R. C. Prog. Heterocycl.c Chem. 1998, 10, 25. (h) Segura, J. L.; Martín, N. Chem. Rev. 1999, 99, 3199.
23. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry, see: (a) Oppolzer, W. Synthesis 1978, 793; Heterocycles 1980, 14, 1615. (b) Kametani, T. Pure Appl. Chem. 1979, 51, 747. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (d) Martín, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237. (e) Chou, T.-S. Rev. Heteroat. Chem. 1993, 8, 65. (f) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (g) Collier, S. J.; Storr, R. C. Prog. Heterocycl.c Chem. 1998, 10, 25. (h) Segura, J. L.; Martín, N. Chem. Rev. 1999, 99, 3199.
24. For reviews of o-quinodimethanes, benzocyclobutenes, and related chemistry, see: (a) Oppolzer, W. Synthesis 1978, 793; Heterocycles 1980, 14, 1615. (b) Kametani, T. Pure Appl. Chem. 1979, 51, 747. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41. (d) Martín, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237. (e) Chou, T.-S. Rev. Heteroat. Chem. 1993, 8, 65. (f) Ando, K.; Kankake, M.; Suzuki, T.; Takayama, H. Tetrahedron 1995, 51, 129. (g) Collier, S. J.; Storr, R. C. Prog. Heterocycl.c Chem. 1998, 10, 25. (h) Segura, J. L.; Martín, N. Chem. Rev. 1999, 99, 3199.
25. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
26. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
27. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
28. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
29. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
30. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
31. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
32. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
33. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
34. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
35. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
36. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
37. For recent works on heterocyclic o-quinodimethanes, see: (a) Tomé, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557. (b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52, 1723; 1996, 52, 1735; 1993, 34, 6639. (c) Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1997, 38, 81. (d) Ohno, M.; Kojima, S.; Shirakawa, Y.; Eguchi, S. Tetrahedron Lett. 1996, 37, 9211; 1995, 36, 6899. (e) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1 1996, 1077 and reference cited therein. (f) Ohno, M.; Koide, N.; Eguchi, S. Heterocycl. Commun. 1995, 1, 125. (g) Ohno, M.; Kojuma, S.; Eguchi, S. J. Chem. Soc., Chem. Commun. 1995, 565. (h) Carly, P. R.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 1995, 36, 2113. (i) Carly, P. R.; Cappelle, S. L.; Compernolle, F.; Hoonaert, G. J. Tetrahedron 1996, 52, 11889. (j) Al Hariri, M.; Jouve, K.; Pautet, F.; Domard, M.; Fenet, B.; Fillion, H. J. Org. Chem. 1997, 62, 405.
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48. Different methods in the synthesis of 31 have been reported, see: (a) Torres-Garcia, G.; Luftmann, H.; Wolff, C.; Mattay, J. J. Org. Chem. 1997, 62, 2752. (b) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C.; de la Cruz, P.; de la Hoz, A.; Langa, F. J. Org. Chem. 1997, 62, 3705. (c) Ohno, M.; Koide, N.; Sato, H.; Eguchi, S. Tetrahedron 1997, 53, 9075.
49. Different methods in the synthesis of 31 have been reported, see: (a) Torres-Garcia, G.; Luftmann, H.; Wolff, C.; Mattay, J. J. Org. Chem. 1997, 62, 2752. (b) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C.; de la Cruz, P.; de la Hoz, A.; Langa, F. J. Org. Chem. 1997, 62, 3705. (c) Ohno, M.; Koide, N.; Sato, H.; Eguchi, S. Tetrahedron 1997, 53, 9075.
50. Different methods in the synthesis of 31 have been reported, see: (a) Torres-Garcia, G.; Luftmann, H.; Wolff, C.; Mattay, J. J. Org. Chem. 1997, 62, 2752. (b) Fernández-Paniagua, U. M.; Illescas, B. M.; Martín, N.; Seoane, C.; de la Cruz, P.; de la Hoz, A.; Langa, F. J. Org. Chem. 1997, 62, 3705. (c) Ohno, M.; Koide, N.; Sato, H.; Eguchi, S. Tetrahedron 1997, 53, 9075.
51. Part of this work has already been presented as follows: (a) In Book of Abstracts; 16th International Congress of Heterocyclic Chemistry, Bozeman, MT, 1997; OP-V-13.
52. (b) Presented at the 216th National Meeting of American Chemical Society, Boston, MA, August 23-27, 1998; Paper 139.
53. 7a however, seemed to fit with the cis- and trans-cylooctenes.
54. (a) Ref 2e.
55. (b) Friebolin, H. Basic One- and Two-Dimensional NMR Spectroscopy; VCH: Weinheim, Germany, 1993; p 293.
56. c‡ values of naphthalene-fused [60]fullerene were reported by Najanyram, Y.; Minowa, T.; Tobita, S.; Shizuka, H.; Nishimura, J. J. Chem. Soc., Perkin Trans. 2 1995, 2351.
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61. For strong evidence of through-space orbital interactions in fulleroids, see: (a) Eiermann, M.; Haddon, R. C.; Knight, B.; Li, Q. C.; Maggini, M.; Martín, N.; Ohno, T.; Prato, M.; Suzuki, T.; Wudl, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1591. (b) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929.
62. For strong evidence of through-space orbital interactions in fulleroids, see: (a) Eiermann, M.; Haddon, R. C.; Knight, B.; Li, Q. C.; Maggini, M.; Martín, N.; Ohno, T.; Prato, M.; Suzuki, T.; Wudl, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1591. (b) Iyoda, M.; Sultana, F.; Sasaki, S.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1994, 1929.
63. For tautomerization of quinoxaline, see: (a) Aumiller, W. D.; Dalton, C. R.; Czarnik, A. W. J. Org. Chem. 1995, 60, 728. (b) Pohmer, J.; Lakshmikantham, M. V.; Cava, M. P. J. Org. Chem. 1995, 60, 8283. (c) Schönberg, A.; Mostafa, A. J. Chem. Soc. 1943, 654.
64. For tautomerization of quinoxaline, see: (a) Aumiller, W. D.; Dalton, C. R.; Czarnik, A. W. J. Org. Chem. 1995, 60, 728. (b) Pohmer, J.; Lakshmikantham, M. V.; Cava, M. P. J. Org. Chem. 1995, 60, 8283. (c) Schönberg, A.; Mostafa, A. J. Chem. Soc. 1943, 654.
65. For tautomerization of quinoxaline, see: (a) Aumiller, W. D.; Dalton, C. R.; Czarnik, A. W. J. Org. Chem. 1995, 60, 728. (b) Pohmer, J.; Lakshmikantham, M. V.; Cava, M. P. J. Org. Chem. 1995, 60, 8283. (c) Schönberg, A.; Mostafa, A. J. Chem. Soc. 1943, 654.