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