Phenacenes: A family of graphite ribbons. 2. Syntheses of some [7]phenacenes and an [11]phenacene by stilbene-like photocyclizations

Journal of the American Chemical Society

Volumn 119, Issue 9, 1997, Pages 2119-2124

  Mallory, Frank B ^a   Butler, Kelly E ^a   Evans, Amanda C ^a   Brondyke, Emilie J ^a   Mallory, Clelia W ^a   Yang, Changqing ^a   Ellenstein, Aviva ^a  

^a BRYN MAWR COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0030931247     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9638418     Document Type: Article

References (20)

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2. (a) For Part 1 in this series, see: Mallory, F. B.; Butler, K. E.; Evans, A. C.; Mallory, C. W. Tetrahedron Lett. 1996, 40, 7173-7176.
3. (b) Mallory, F. B.; Butler, K. E.; Evans, A. C.; Mallory, C. W. 1995 International Chemical Congress of Pacific Basin Societies, Abstract #3294.
4. (c) Butler, K. E. M.A. Thesis, Bryn Mawr College, 1996.
5. We are grateful to Dr. Andrew R. McGhie of the University of Pennsylvania for determining the melting behavior of [7]phenacene (1) by differential scanning calorimetry.
6. 1,2,4,5-Tetrachloro-3,6-dideuteriobenzene was prepared for use as a high-temperature NMR solvent as described in the following: Zimmerman, H. Mol. Cryst. Liq. Cryst. 1978, 49, 1-5.
7. 2.
8. 2 by irradiation with visible light) to isomerize these product mixtures in cyclohexane solution to the thermodynamically favored E isomer, which is then recrystallized to high purity. Although stilbene-like photocyclization ultimately requires absorption of an ultraviolet photon by the Z isomer, either the E or the Z isomer can be used as the starting material because they are interconverted by ultraviolet irradiation. It is sometimes convenient to carry out photocyclizations starting with the E,Z mixture that is obtained from a Wittig reaction.
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