PDF herunterladen
Synthesis 2005(3): 470-474  
DOI: 10.1055/s-2005-861799
PAPER
© Georg Thieme Verlag Stuttgart · New York

The Synthesis, Structural Characterization and Photochemistry of Some 3-Phenylindenones

Michael K. Seery, Sylvia M. Draper, John M. Kelly*, Thomas McCabe, T. Brian H. McMurry*
Chemistry Department, Trinity College, Dublin 2, Ireland
Fax: +353(1)6712826; e-Mail: jmkelly@tcd.ie; e-Mail: tmcmurry@tcd.ie ;
Weitere Informationen

Publikationsverlauf

Received 13 September 2004
Publikationsdatum:
26. Januar 2005 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

The synthesis of 3-phenylindenone (1a), 6-methoxy-3-phenylindenone (1b), 2-bromo-6-methoxy-3-phenylindenone (1c) and 2-ethoxycarbonyl-6-methoxy-3-phenylindenone (1d) is described using two methods - synthesis via indanone precursors and synthesis via propanedione precursors. Crystal structures of 2-bromo-6-methoxy-3-phenylindanone, the synthetic precursor to 1b and 2-bromo-6-methoxy-3-phenylindenone were obtained. Preliminary photochemical studies showed that 1b dimerizes readily, but no transient species were detectable using ns-flash photolysis.

Key words

enone - [2+2] cycloaddition - Friedel-Crafts ring closure - photochemistry

    References

  • 2 Bensasson RV. Land EJ. Truscott TG. Excited States and Free Radicals in Biology and Medicine   Oxford University Press; New York: 1993. 
    Google Scholar
  • 3 Kelly JFD. Kelly JM. McMurry TBH. J. Chem. Soc., Perkin Trans. 2  1999,  1933 
    CrossrefGoogle Scholar
  • 4 Murphy WS. Wattansin S. J. Chem. Soc., Perkin Trans. 1  1980,  1555 
    CrossrefGoogle Scholar
  • 5 Gaviña F. Costero AM. González AM. J. Org. Chem.  1990,  55:  2060 
    CrossrefGoogle Scholar
  • 6 Anstead GM. Srinivasan R. Peterson CS. Wilson SR. Katzenellenbogen JA. J. Am. Chem. Soc.  1991,  113:  1378 
    CrossrefGoogle Scholar
  • 8 McMurry TBH. Murphy AG. Work DN. Avent AG. James JP. J. Chem. Res., Synop.  2002,  7:  317 
    Google Scholar
1

Current Address: School of Chemistry, Dublin Institute of Technology, Kevin St., Dublin 8, Ireland.

7

Full crystal structure data have been deposited with the Cambridge Crystallographic Data Centre. Deposition numbers are 249671 and 249672 for 4 and 1c, respectively.