Phenacenes: A family of graphite ribbons. 1. Syntheses of some [7]phenacenes by stilbene-like photocyclizations

Tetrahedron Letters

Volumn 37, Issue 40, 1996, Pages 7173-7176

  Mallory, Frank B ^a   Butler, Kelly E ^a   Evans, Amanda C ^a   Mallory, Clelia W ^b  

^a BRYN MAWR COLLEGE   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0030607230     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01618-8     Document Type: Article

References (10)

1. 1. (a) Presented in part at the 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, December 17-22, 1995, paper #3294, and at the 31st Middle Atlantic Regional Meeting of the American Chemical Society, Villanova, Pennsylvania, May 22, 1996, paper #145.
2. (b) Taken in part from the M.A. Thesis of Kelly E. Butler, Bryn Mawr College, 1996.
3. 2. Mallory, F. B.; Mallory, C. W. Organic Reactions 1984, 30, 1-456.
4. 18: C, 95.21; H, 4.79. Found: C, 95.21; H, 4.75.
5. 4. For convenience the stilbene analogs in Schemes 1-3 are depicted as Z isomers. Actually, the Wittig reactions shown in these Schemes produce mixtures of E and Z isomers. For purposes of purification and characterization of the Wittig product we routinely isomerize these mixtures entirely to the E isomer by treatment with iodine and visible light. The ultraviolet light that photocyclizes the Z isomer of a stilbene analog also interconverts its E and Z isomers, so either isomer can serve as the starting material for a photocyclization; it is often convenient to use the E,Z mixture obtained from the Wittig reaction.
6. 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.
7. 38: C, 92.62; H, 7.38. Found: C, 92.62; H, 7.07.
8. 34: C, 93.02; H, 6.98. Found: C, 92.62; H, 7.20.
9. 8. Elemental analyses were performed by M-H-W Laboratories, P.O. Box 15149, Phoenix, AZ 85018.
10. 9. Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769-3775.