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Organic Chemistry 2

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Ketone to Amide with Azide Mechanism

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What is the most reasonable mechanism for the conversion of Compounds A and B in the presence of a Lewis acid catalyst into ring-expanded amide Compound C, accompanied by $N_2$ gas?

Compounds A-C are the same in all of the answer choices. This reaction is known as the azido-Schmidt reaction, which has some mechanistic and atom reorganization similarity with the Bayer-Villiger reaction. Some basic information about the Lewis acid and resonance interactions in azides are depicted below.

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A

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B

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C

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D

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