Diphenylacetylene

Diphenylacetylene

Automated Computation for a Single Reaction

Published in John Andraos, Reaction Green Metrics, 2018

Benzil is prepared from diphenylacetylene via oxidation under microwave irradiation conditions in dimethylsulfoxide with iodine as catalyst. Experimental data for the yield of benzil with catalyst loading is shown in the table below.

Scholl reaction of hexaphenylbenzenes with hexakis-alkoxy substituents

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Journal Information

Published in Liquid Crystals, 2019

Shilpa Setia, Sandeep Kumar, Debashis Adhikari, Santanu Kumar Pal

The synthesis of a prototypical HBC precursor 1a started from the alkylation of commercially available 4-bromocatechol with 1-bromooctane to give compound 4a in quantitative yield (Scheme 1). The Stille-type coupling of 4a with bis(tributylstannyl)acetylene and Pd(PPh3)4 in toluene gave the corresponding symmetrical diphenylacetylenes 5a in 55% yield. Subsequent cyclotrimerisation of the diphenylacetylene 5a with [Co2(CO)8] in 1,4-dioxane yielded the hexaphenylbenzene precursor molecule 1a in 49% yield. The synthetic details of various Scholl precursors in Chart 1 and their spectroscopic characterisation (1H and 13C NMR, IR and MALDI mass spectrometry) are presented in the experimental section.

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Automated Computation for a Single Reaction

Scholl reaction of hexaphenylbenzenes with hexakis-alkoxy substituents