Mechanism of the Chapman rearrangement of N-arylbenzimidates on the basis of a molecular structure established by X-ray crystallography
Abstract
The crystal and molecular structure of 2-methoxycarbonyl-1-naphthyl N-(1-naphthyl)benzimidate (11), which gives dibenz[ch]acridinone (13) in the Chapman rearrangement, has been determined by X-ray diffraction. The mechanism of the Chapman rearrangement can be interpreted on the basis of the X-ray data, in particular the observation of a non-bonded N ⋯ C interaction (2.648 Å).