An Annulene-Fused Cyclopentadienide. A Photochromic Cyclopentadienodimethyldihydropyrene Where the Fused Cyclopentadienide Group Resembles Benzene in Its Effect on the Dihydropyrene-Metacyclophanediene Valence Isomerization

Journal of Organic Chemistry

Volumn 69, Issue 2, 2004, Pages 549-554

  Mitchell, Reginald H ^a   Fan, Wei ^a   Lau, Danny Y K ^a   Berg, David J ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; IRRADIATION; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS (CHEMICAL); ULTRAVIOLET RADIATION;

PHOTOSWITCHING;

PHOTOCHROMISM;

ANION; BENZENE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; CYCLOPENTADIENODIMETHYLDIHYDROPYRENE; DIHYDROPYRENE; DIMETHYLDIHYDROPYRENE; METACYCLOPHANEDIENE; PROTON; PYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; IRRADIATION; ISOMERISM; LIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 0347132674     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0354589     Document Type: Article

References (16)

1. Garratt, P. J. In Aromaticity; Wiley-Interscience: New York, 1986; Chapter 5. Lloyd, D. In Nonbenzenoid conjugated carbocyclic compounds; Elsevier: Amsterdam, The Netherlands, 1984; Chapter 2.
2. Garratt, P. J. In Aromaticity; Wiley-Interscience: New York, 1986; Chapter 5. Lloyd, D. In Nonbenzenoid conjugated carbocyclic compounds; Elsevier: Amsterdam, The Netherlands, 1984; Chapter 2.
3. Thiele, J. Ber. 1901, 34, 68.
4. Mitchell, R. H.; Khalifa, N. A.; Dingle, T. W. J. Am. Chem. Soc. 1991, 113, 6696-6697.
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7. Mitchell, R. H. Eur. J. Org. Chem. 1999, 2695-2703.
8. Mitchell, R. H.; Ward, T. R.; Chen, Y.; Wang, Y.; Weerawarna, S. A.; Dibble, P. W.; Marsella, M. J.; Almutairi, A.; Wang, Z. Q. J. Am. Chem. Soc. 2003, 125, 2974-2988.
9. An improved large-scale preparation of 3 is given in the Supporting Information of ref 7.
10. Miyazawa, A.; Yamato, T.; Tashiro, M. J. Org. Chem. 1991, 56, 1334-1337.
11. Sheepwash, M. A.; Mitchell, R. H.; Bohne, C. J. Am. Chem. Soc 2002, 124, 4693-4700.
12. Schmidt, W. Helv. Chim. Acta. 1971, 54, 862-868. Schmidt, W. Tetrahedron. Lett. 1972, 12, 581-584.
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14. Dr. R. V. Williams (University of Idaho), who has considerable experience in DHP calculations, is attempting to model this process.
15. Sheepwash, M. A.; Ward, T. R.; Wang, Y.; Bandyopadhyay, S.; Mitchell, R. H.; Bohne, C. Photochem. Photobiol. Sci. 2003, 2, 104-122.
16. Bens, A. T.; Frewert, D.; Kodatis, K.; Ktyschi, C.; Martin, H-D.; Trommsdorff, H. P. Eur. J. Org. Chem. 1998, 2333-2338.