Journal of the Chemical Society. Perkin transactions I p. 1367 - 1370 (1981)
Update date:2022-07-30
Topics: Rearrangement Heterocycles
Sarlo, Francesco De
Guarna, Antonio
Mascagni, Paolo
Carrie, Robert
Guenot, Pierre
N-Substituted hydroxylamines (2) add to 2-benzoyl-N,2-diphenylvinylideneamine (1) and the adducts are easily dehydrated to give the 3-iminoisoxazolines (4).Compounds (4) with 2-aryl substituents rearrange spontaneously to give the 2-imino-oxazolines (5) or (6), but the 2-methyl derivative is more stable and only rearranges on heating. 2-Imino-3-acylaziridines (8) or (9) are assumed to be the intermediates; the expected 2-imino-oxazoline (5b) was isolated among the products during an attempted synthesis of 1,3-diphenyl-2-phenylimino-3-benzoylaziridine (8b) from benzoylphenylcarbene and diphenylcarbodi-imide.
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