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Published December 26, 1997 | Supplemental Material
Journal Article Open

Synthesis of Substituted Bicyclo[2.2.2]octatrienes


An efficient route to bicyclo[2.2.2]octatriene, barrelene, and substituted versions of this molecule has been developed starting from the benzene equivalent cis-3,5-cyclohexadiene-1,2-diol. Following the Diels−Alder reaction of this molecule with an activated acetylene, conversion of the diol to the final olefin was accomplished through formation of a thiocarbonate intermediate and subsequent reaction with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine (DPD). The synthesis developed allows a variety of barrelenes to be prepared in as few as three steps from commercially available starting materials.

Additional Information

© 1997 American Chemical Society. Received June 10, 1997. Publication Date (Web): December 26, 1997. Financial support for this research was provided by the Office of Naval Research, the U.S. Air Force, and the Ballistic Missiles Defense Organization through an AASERT grant. We also thank Dr. D. G. H. Ballard and ICI for their gift of cis-3,5-cyclohexadiene-1,2-diol.

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