An Electron Diffraction Investigation of Biphenylene

Abstract

W. C. Lothrop has synthesized an aromatic hydrocarbon C_(12)H_8 to which he assigns the structure (I) and the name biphenylene. It was thought worth while to establish the structure of Lothrop's biphenylene by other than chemical means. In this we have succeeded, mainly by the electron diffraction investigation described below. Our work confirms structure (I) and in particular rules out structure (II) [chemical structure] which has been proposed by W. Baker and supported by C. A. Coulson . Biphenylene and its derivatives synthesized by Lothrop are thus the first molecules of definitely established structure to contain the interesting aromatic four-ring. They should prove very valuable for studies of orientation effects due to conjugation and to strains of the bond angles (Mills-Nixon effect). Our investigations were carried out with a 1.5-g. sample of the compound, kindly given to us by Dr. Lothrop.

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