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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 6
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Original Articles

Synthesis of Bicyclo[4.3.0]Non-3-ene-7,9-diones via Solventless Diels–Alder Methodology

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Pages 898-902 | Received 10 Sep 2009, Published online: 25 Feb 2011
 

Abstract

Four novel bicyclo[4.3.0]non-3-ene-7,9-diones have been synthesized in moderate to good yields through a solventless Diels–Alder cycloaddition method and characterized. Atom economies after purification ranged from 21% to 32%, and E factors ranged from 2.7 to 3.7. All reaction products exhibited endo selectivity. Dienophiles with heteroatoms that contribute electrons to the π system exhibited faster reaction times than the carbocyclic analog. Hydrogen-bond donating ability in the diene had no noticeable effect on reaction times.

ACKNOWLEDGMENTS

The Mass Spectrometry Laboratory at the University of Illinois–Urbana/Champaign provided high-resolution mass spectra. NMR Analysis and Consulting of Decatur, Illinois, provided high-field NMR spectra. The FTIR spectrophotometer was acquired with partial funding from a 2008 Pittsburgh Conference Memorial National College Grant. The authors thank Dr. Clarence Josefson for performing MO energy calculations.

Notes

a Although not formally a reactant, the rinse solvent was included in the calculation of atom economy.

b Ref. 19.

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