Completely regioselective, highly stereoselective syntheses of cis-Bisfullerene[60] adducts of 6,13-disubstituted pentacenes

Organic Letters

Volumn 2, Issue 25, 2000, Pages 3979-3982

  Miller, Glen P ^a   Mack, James ^a  

^a Univ of New Hampshire   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003422565     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0064718     Document Type: Article

References (11)

1. Mack, J.; Miller, G. P. Fullerene Sci., Technol. 1997, 5, 607.
2. Gribble, G.; Allen, R. W. Tetrahedron Lett. 1976, 3673.
3. Murata, Y.; Kato, N.; Fujiwara, K.; Komatsu, K. J. Org. Chem. 1999, 64, 3483.
4. (a) Stewart, J. J. P. Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH Publishers: New York, 1990; pp 45-81.
5. (b) Thiel, W. Tetrahedron 1988, 44, 7393.
6. (a) Allen, C. F. H.; Bell, A. J. Am. Chem. Soc. 1942, 64, 1253.
7. (b) In our investigations, we observe formation of both endo-and exo-maleic anhydride monoadducts of 6,13-diphenylpentacene, but with cycloaddition occurring exclusively across the 5,14-pentacene carbons.
8. 2-or KI-promoted aromatization of the corresponding diol. See ref 4. The stability of the 6,13-disubstituted pentacenes varies as a function of substitution. Oxidation and/or photodimerization are common degradation paths.
9. MeOH solutions of 7 were employed for electrospray MS experiments. While excellent results could be obtained with polar diol 7, nonpolar hydrocarbon 6 showed poor solubility in MeOH and gave unsatisfactory results.
10. (a) Anker, W.; Beveridge, K. A.; Bushnell, G. W.; Mitchell, R. H. Can. J. Chem. 1984, 62, 661.
11. (b) Mitchell, R. H.; Anker, W. Tetrahedron Lett. 1981, 5135.