Tetrahedron Letters p. 5537 - 5540 (1984)
Update date:2022-08-04
Topics:
Endo, Yasuyuki
Terashima, Tohru
Shudo, Koichi
In the presence of trifluoroacetic acid, N-phenyl-N'-phenoxyurea (1a) rearranges to N-(4'-hydroxy-2-biphenylyl)urea (2a) and N-carbamoyl-2-hydroxy-diphenylamine (3a).The rearrangement is an intramolecular reaction, and the transition state of the breakage of the N-O bond is deduced to be polarized in the form Nδ+(*)Oδ+.
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