Exohedral functionalization of [60]fullerene by [4+2] cycloadditions. Diels-Alder reactions of [60]fullerene with electron rich 2,3-dioxy-substituted-1,3-butadienes

Tetrahedron

Volumn 52, Issue 15, 1996, Pages 5421-5426

  Torres García, Gregorio ^a,b   Mattay, Jochen ^a,b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b UNIVERSITY OF KIEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXANE DERIVATIVE; 1,3 DIOXOLANE DERIVATIVE; FULLERENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0029923858     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00172-X     Document Type: Article

References (17)

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3. Recents reviews: a) Hirsch, A. in The Chemistry of the Fullerenes, Thieme, Stuttgart, 1994.
4. b) Hirsch, A. Synthesis, 1995, 895-913.
5. a) Averdung, J.; Budwach, T.; Iwanek, W.; Schlachter, I.; Torres-Garcia, G.; Mattay, J. in Physics and Chemistry of Fullerenes and Derivatives, Kuzmany, H.; Fink, J.; Mehring, M.; Roth, S. Editors, 1995, 137-141.
6. b) Averdung, J.; Luftmann, H.; Mattay, J.; Claus, K.-U.; Abraham, W. Tetrahedron Lett. 1995, 36, 2957-2958.
7. c) Averdung, J.; Mattay, J.; Jacobi, D.; Abraham, W. Tetrahedron, 1994, 51, 2543-2552
8. a) Ref. 2a, Chapter 4 and 2b. For a recent application of high pressure Diels-Alder: Takeshita, H.; Liu, J.-F.; Kato, N.; Mori, A.; Isobe, R. Chem. Lett. 1995, 5, 377-378.
9. a) Lamparth, I.; Maichle-Mössmer, C.; Hirsch, A. Angew. Chem. 1995, 107, 1755-1757; Angew. Chem. Int. Ed. Engl. 1995, 34, 1607-1609.
10. a) Lamparth, I.; Maichle-Mössmer, C.; Hirsch, A. Angew. Chem. 1995, 107, 1755-1757; Angew. Chem. Int. Ed. Engl. 1995, 34, 1607-1609.
11. b) Kräutler, B.; Maynollo, J. Angew. Chem., 1995, 107, 69-71; Angew. Chem. Int. Ed. Engl. 1995, 34, 87-88.
12. b) Kräutler, B.; Maynollo, J. Angew. Chem., 1995, 107, 69-71; Angew. Chem. Int. Ed. Engl. 1995, 34, 87-88.
13. Scharf, H.-D.; Plum, H.; Fleischhauer, J.; Schlecker, W. Chem. Ber. 1979, 112, 862-882.
14. The fast ring inversion had been observed with analogous system: Kräutler, B.; Puchberger, M. Helv. Chim. Acta, 1993, 76, 1626-1631; Ganapathi, P.S.; Friedman, S.H.; Kenyon, G.L.; Rubin, Y. J. Org. Chem., 1995, 60, 2954-2955 and Ref 5b.
15. The fast ring inversion had been observed with analogous system: Kräutler, B.; Puchberger, M. Helv. Chim. Acta, 1993, 76, 1626-1631; Ganapathi, P.S.; Friedman, S.H.; Kenyon, G.L.; Rubin, Y. J. Org. Chem., 1995, 60, 2954-2955 and Ref 5b.
16. 3SiI without results.
17. 2 atmosphere and protected from light, but only traces of the monoadduct were detected by HPLC.