Journal of the Chemical Society. Perkin transactions II p. 2093 - 2098 (1988)
Update date:2022-08-02
Topics:
Boyd, A. John
Boyd, Derek R.
Burnett, Michael G.
Malone, John F.
Jennings, W. Brian
The dinitrone derivatives (5a, b) of 2,2,4,4-tetramethylcyclobutane-1,3-dione were synthesised by peroxyacid oxidation of the corresponding di-imines (3a, b).X-ray crystallographic analysis of diimine (3a) and the hydroxyimino nitrone isomers (6a, b) indicate a marked buttressing effect leading to an exclusive preference for the trans geometry in di-imine (3a) and dinitrone (5a).Thermal elimination reactions of the N-But substituted nitrones (5a), (6a), and (8a) to yield oximes and 2-methylpropene have been investigated bu u.v. kinetic studies.The results areconsistent with a concerted mechanism involving a five-membered cyclic transition state.
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