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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 ;
Further Information

Publication History

Received 13 September 2004
Publication Date:
26 January 2005 (online)

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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

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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.