The Rearrangement of Diphenyl

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We wish to report unequivocal evidence for the water promoted, aluminum chloride induced intramolecular rearrangement of the benzene rings in diphenyl. When diphenyl 1→1,1'-C14, prepared in 80% yield via an Ullmann reaction on iodobenzene-1-C1 14, was heated to 100° for 30 min. with 10 mole % of aluminum chloride and 1 mole % of water, the radioactivity, originally localized at the two connecting carbons had been randomly distributed. Recovered active diphenyl was also shown to be randomized when the reaction was carried out for 12 hrs. in a refluxing benzene solution. The degradation method used is outlined in Fig. 1. … continued below

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Wynberg, Hans & Wolf, A. P. October 15, 1963.

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We wish to report unequivocal evidence for the water promoted, aluminum chloride induced intramolecular rearrangement of the benzene rings in diphenyl. When diphenyl 1→1,1'-C14, prepared in 80% yield via an Ullmann reaction on iodobenzene-1-C1 14, was heated to 100° for 30 min. with 10 mole % of aluminum chloride and 1 mole % of water, the radioactivity, originally localized at the two connecting carbons had been randomly distributed. Recovered active diphenyl was also shown to be randomized when the reaction was carried out for 12 hrs. in a refluxing benzene solution. The degradation method used is outlined in Fig. 1. The view that the reaction in intramolecular is supported by the following facts: (1) The inactive benzene used in the solvent experiments was devoid of activity at the end of a run within the precision of our assay methods. A rearrangement carried out with inactive diphenyl in benzene-1-C- 14 yielded diphenul having an activity indicating less than 0.001% intermolecularity.

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  • October 15, 1963

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  • Feb. 5, 2022, 9:58 a.m.

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Wynberg, Hans & Wolf, A. P. The Rearrangement of Diphenyl, report, October 15, 1963; Washington D.C.. (https://digital.library.unt.edu/ark:/67531/metadc1255884/: accessed July 18, 2025), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT Libraries Government Documents Department.

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