Cobalt-Catalyzed [2+2+2] Cycloaddition of Phenylacetylene with 1,3-Dienes for the Synthesis of Vinyl-Substituted 1,4-Diphenylcyclohexa-1,3-dienes

 

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Abstract

The cobalt-catalyzed [2+2+2] cycloaddition of two alkynes and a 1,3-diene, utilizing either a dibromo[1,2-bis(diphen­ylphosphino)]benzene cobalt or a dibromobis(triphenylphosphino)cobalt complex, under reductive conditions gives vinyl-substituted cyclohexa-1,3-diene derivatives in acceptable yields. The oxidation of 5-methyl-1,4-diphenyl-5-vinylcyclohexa-1,3-diene by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone leads to a rearrangement resulting in a vinyl-terphenyl derivative.

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The ratios were determined by GC/GCMS analysis. The missing percentages result from unidentified side products.

CCDC 659433 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

The quality of the crystal was significantly reduced by disordered solvent within the crystal cell.

The R _f values of TLC analysis utilizing pentane as the eluent span a range between 0.75 and 0.90.

¹H NMR data were assigned of the major component to the best of our knowledge and ¹³C NMR and HRMS data were not obtained based on the low purity of the sample.