Oxoketene–oxoketene, imidoylketene–imidoylketene and oxoketenimine–imidoylketene rearrangements. 1, 3-Shifts of phenyl groups

…, KP Netsch, G Penn, G Kollenz, C Wentrup

Index: George, Lisa; Netsch, Klaus-Peter; Penn, Gerhard; Kollenz, Gert; Wentrup, Curt Organic and Biomolecular Chemistry, 2006 , vol. 4, # 3 p. 558 - 564

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Citation Number: 25

Abstract

Dibenzoylketene 5 undergoes degenerate 1, 3-shifts of the phenyl group between acyl and ketene carbon atoms, thus interconverting it with 6 and 7. This 1, 3-shift takes place in the gas phase under flash vacuum thermolysis (FVT) conditions, but not in solution at 110–145° C. Imidoyl (benzoyl) ketene 13 undergoes degenerate 1, 3-shift of the phenyl group on FVT, thus interconverting it with 14, but the ketenimine isomer 15 is not formed, and none of ...