Anomalous results were obtained when γ-phenylbutyric acid (I) was subjected to the Schmidt reaction. 4,5-Dihydro-1H-1-benzazepin-2(3H)-one (IX) was obtained in 40% yield besides 4-(3-aminopropyl)benzenesulphonic acid (III). The structure of (III) was established by chemical degradation. No cyclic lactams are formed under the same conditions from higher and lower homologues of (I).
S. K. Datta, C. Grundmann and N. K. Bhattacharyya, J. Chem. Soc. C, 1970, 2058 DOI: 10.1039/J39700002058
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