The Constitution of Pirylene: Chemical Evidence

Abstract

A sample of this hydrocarbon has been submitted to Dr. V. Schomaker and Dr. R. Spurr of these Laboratories who have been able to work out its structure from the electron diffraction pattern. Their investigation indicates that (IV) is not a ring compound, but possesses the structure (V) of 1-methyl-2-vinylacetylene, a known substance, the physical properties of which agree well with those of pirylene. The results of our chemical investigation are in full conformity with this conclusion. On catalytic reduction pirylene readily took up three moles of hydrogen; the reduced product was shown to be n-pentane. It also added one mole of hydrogen chloride, as has been demonstrated for (V), giving 3-chloro-1,3-pentadiene (methylchloroprene) (VI).

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