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

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

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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.