Synthesis of Substituted Bicyclo[2.2.2]octatrienes
The Journal of Organic Chemistry1997Vol. 62(26), pp. 9076–9082
Citations Over Time
Abstract
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.
Related Papers
- → Stability Relationships in Bicyclic Ketones(2005)60 cited
- → Drastic ring transformation reactions of fused bicyclic rings to bridged bicyclic rings(1992)11 cited
- → Infrared Spectra of Acetylene and Acetylene Derivatives Adsorbed on Alumina and Silica(1961)58 cited
- → Herstellung der reinen, bicyclischen Olefine Bicyclo[4.2.1]non‐2‐en, Bicyclo[4.2.1]non‐3‐en und Bicyclo[4.2.1]non‐7‐en(1979)5 cited
- → OPTIMIZATION OF TECHNOLOGICAL PARAMETERS OF HYDRAGENERATION PROCESS OF ACETYLENE USING A PILOT CATALYTIC PLANT(2020)