Weerman degradation on alpha-hydroxy amides

I came across this reaction scheme in the solutions of a test paper:


[![Weerman degradation](https://i.stack.imgur.com/eqjkD.png)](https://i.stack.imgur.com/eqjkD.png)


I understand the formation of isocyanate intermediate as the first step. In the second step, I realized that hydrolysis will be more favourable at the benzyl carbon, hence forming benzaldehyde (given as the major product).


However, I cannot understand how aniline is being formed. There must be another migration/rearrangement occurring, but I cannot figure out how. It might be some reaction I am unaware of.




Since OP did not give any reference to the rearrangement in the question, I doubted the formation of aniline is true even if as a minor product. The conversion of $\alpha$-hydroxy amides to corresponding aldehydes is a well-known degradation reaction, commonly known as [Weerman degradation](https://en.wikipedia.org/wiki/Weerman_degradation):
$$\ce{R-CH(OH)-C=O-NH2 ->[NaOBr][\Delta] RCHO + H2NCO2H}$$
Although this degradation is independently discovered (Ref.1), Some authors have regarded it as an extension of the Hofmann rearrangement (Ref.2) because of the similarity in proposed mechanism:


[![Weerman degradation](https://i.stack.imgur.com/T8CCI.jpg)](https://i.stack.imgur.com/T8CCI.jpg)


Accordingly, to my knowledge, there is no place to have an rearrangement other than proposed. However, even if it is most unlikely, there could be a possibility to have 1,3-phenyl shift at the intermediate $\bf{I}$ stage:


[![Phenyl a-ketoamide formation](https://i.stack.imgur.com/nkBNU.jpg)](https://i.stack.imgur.com/nkBNU.jpg)


The resultant phenyl $\alpha$-ketoamide could undergoes base hydrolysis under the reaction condition to give aniline.


**Note:** The 1,3-phenyl shift has been known for other reactions (Ref.3).


**References:**


1. R. A. Weerman, "Sur une synthèse d'aldéhydes et de l'indol," *Recueil des Travaux Chimiques des Pays-Bas et de la Belgique* **1910**, *29(1-2)*, 18-21 (DOI: <https://doi.org/10.1002/recl.19100290104>).
2. C. L. Arcus and D. B. Greenwood, "398. The Hofmann reaction with α- and β-hydroxy-amides: reactions of the intermediate isocyanates," *J. Chem. Soc.* **1953**, 1937-1940 (DOI: <https://doi.org/10.1039/JR9530001937>).
3. Colin Eaborn, Karen L. Jones, Paul D. Lickiss, and Włodzimierz A. Stańczyk, "Proportion of 1,3-phenyl migration in trifluoroethanolysis, methanolysis, and hydrolysis of $\ce{(Me3Si)2C(SiMe2Ph)(SiEt2I)}$," *J. Chem. Soc., Perkin Trans. 2* **1993**, *(3)*, 395-397 (DOI: <https://doi.org/10.1039/P29930000395>).


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