Sequential multiple-photon photochemistry of sterically congested enones

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2317-2320

  Schnapp, Karlyn A ^a   Motz, Philip L ^a   Stoeckel, Sharon M ^a   Wilson, R Marshall ^b   Krause Bauer, Jeanette A ^b   Bohne, Cornelia ^c  

^a NORTHERN KENTUCKY UNIVERSITY   (United States)

^b UNIVERSITY OF CINCINNATI   (United States)

^c UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CYCLIZATION; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029930478     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00284-5     Document Type: Article

References (15)

1. Schuster, D. I. In The Chemistry of Enones, Part 2, Patai, S.; Rappoport, Z., Ed.; John Wiley and Sons: New York, NY, 1989; pp 623-756 and references contained therein.
2. Similar transformations have been reported by Terpetschnig, E.; Penn, G.; Kollenz, G.; Peters, K.; Peters, E. M. Tetrahedron, 1991, 47, 3045.
3. 3, Z = 4, T = 25°C, 2287 observed reflections (F>3.0σ(F)), diffractometer and solution as for 4 to obtain a final R = 5.79%, wR = 5.98% and a goodness of fit of 1.39.
4. Calculations were conducted using Hyperchem, release 2, on a Silicon Graphics Indigo XS24 4000. Minimizations and energy calculations were conducted using AM1, UHF or RHF, to gradients of <0.03 kcal/(Å-mol).
5. Wilson, R. M.; Hannemann, K.; Schnapp, K. A.; Memarian, H. R.; Azadnia, A. SPSE Proc. Summer Symp. Photochem. Imaging, 1988, 167. Wilson, R. M.; Schnapp, K. A.; Hannemann, K.; Ho, D. M.; Memarian, H. R.; Azadnia, A.; Pinhas, A. R.; Figley, T. M. Spectrochim. Acta, 1990, 46A, 551. Wilson, R. M.; Adam, W.; Schulte Oestrich, R. The Spectrum 1991, 4, Fall Issue, 8. Wilson, R. M.; Schnapp, K. A. Chem. Rev. 1993, 93, 223.
6. Wilson, R. M.; Hannemann, K.; Schnapp, K. A.; Memarian, H. R.; Azadnia, A. SPSE Proc. Summer Symp. Photochem. Imaging, 1988, 167. Wilson, R. M.; Schnapp, K. A.; Hannemann, K.; Ho, D. M.; Memarian, H. R.; Azadnia, A.; Pinhas, A. R.; Figley, T. M. Spectrochim. Acta, 1990, 46A, 551. Wilson, R. M.; Adam, W.; Schulte Oestrich, R. The Spectrum 1991, 4, Fall Issue, 8. Wilson, R. M.; Schnapp, K. A. Chem. Rev. 1993, 93, 223.
7. Wilson, R. M.; Hannemann, K.; Schnapp, K. A.; Memarian, H. R.; Azadnia, A. SPSE Proc. Summer Symp. Photochem. Imaging, 1988, 167. Wilson, R. M.; Schnapp, K. A.; Hannemann, K.; Ho, D. M.; Memarian, H. R.; Azadnia, A.; Pinhas, A. R.; Figley, T. M. Spectrochim. Acta, 1990, 46A, 551. Wilson, R. M.; Adam, W.; Schulte Oestrich, R. The Spectrum 1991, 4, Fall Issue, 8. Wilson, R. M.; Schnapp, K. A. Chem. Rev. 1993, 93, 223.
8. Wilson, R. M.; Hannemann, K.; Schnapp, K. A.; Memarian, H. R.; Azadnia, A. SPSE Proc. Summer Symp. Photochem. Imaging, 1988, 167. Wilson, R. M.; Schnapp, K. A.; Hannemann, K.; Ho, D. M.; Memarian, H. R.; Azadnia, A.; Pinhas, A. R.; Figley, T. M. Spectrochim. Acta, 1990, 46A, 551. Wilson, R. M.; Adam, W.; Schulte Oestrich, R. The Spectrum 1991, 4, Fall Issue, 8. Wilson, R. M.; Schnapp, K. A. Chem. Rev. 1993, 93, 223.
9. a] photocycloaddition.
10. For further mechanistic studies of the photoreactions of enone 1, see: Schnapp, K. A.; Motz, P. L.; Wilson R. M.; Winter, D.; Krause Bauer, J. A. Tetrahedron Lett. submitted for publication.
11. Enone 2 was prepared using a modification of the procedure of House (House, H. O.; Reif, D. J. J. Am. Chem.Soc. 1955, 77, 6525) to produce the alcohol which was subsequently oxidized with PCC to produce the enone.
12. Muszkat, K. A.; Fischer, E. J. Chem. Soc. B 1967, 662. Repinec, S. T.; Sension, R. J.; Szarka, A. Z.; Hochstrasser, R. M. J. Phys. Chem. 1991, 95, 10380.
13. Muszkat, K. A.; Fischer, E. J. Chem. Soc. B 1967, 662. Repinec, S. T.; Sension, R. J.; Szarka, A. Z.; Hochstrasser, R. M. J. Phys. Chem. 1991, 95, 10380.
14. In laser flash photolysis studies, the samples were excited with either an excimer laser at 308 nm (Lumonics EX-510) or with a YAG laser at 266 nm (Spectra Physics GCR 12) in acetonitrile. The analyzing beam consisted of a pulsed 150W Xe lamp and light intensities were detected by a photomultiplier/monochromator system. Signals were captured on a Tektronix TDS 520 digital scope. The experimental set-up was integrated to a MacIntosh IICi and the programs for data acquisition and analysis were written in Labview 2.2. A flow system was employed to insure that for each laser pulse a fresh sample was irradiated. Similar spectra were obtained in benzene with 308 nm excitation.
15. While no phenanthrene cyclization was observed when 1 was irradiated in benzene, the phenanthrene corresponding to 9 was isolated when 1 was irradiated in methanol, see ref. 7.