Chapman Rearrangement

O. Mumm et al., Ber. 48, 379 (1915); A. W. Chapman, J. Chem. Soc. 127, 1992 (1925); 1927, 174; 1929, 569.

Thermal rearrangement of aryl imidates to N,N-diaryl amides:



J. W. Schulenberg et al., Org. React. 14, 1 (1965); C. G. McCarty, L. Garner in The Chemistry of Amidines and Imidates S. Patai, Ed. (Interscience, New York, 1975) p 189. Mechanistic study: N. A. Suttle, A. Williams, J. Chem. Soc. Perkin Trans. II 1983, 1369. Synthetic applications: L. H. Peterson et al., J. Heterocyclic Chem. 18, 659 (1981); N. Dubau-Assibat et al., Bull. Soc. Chim. Fr. 132, 1139 (1995). Chapman-like rearrangements: F. Esser et al., J. Chem. Soc. Perkin Trans. I 1988, 3311; M. Dessolin et al., Chem. Commun. 1992, 132.