The synthesis of 2-N-acylamino-substituted benzylcyclopropanes has been carried out. It was established that under the action of acids 2-N-acylamino-substituted benzylcyclopropanes are rearranged into the corresponding 4H-3, 1-benzoxazines and not into the expected 3, 1-benzoxazepines. It was shown that a similar type of rearrangement is also characteristic for 2-N-acylamino-substituted allylbenzenes.