Issue 0, 1981
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Base catalysed rearrangements involving ylide intermediates. Part 13. Further rearrangements of 2-oxidoanilinium ylides

W. David Ollis,   Ratnasamy Somanathan  and  Ian O. Sutherland  

Abstract

The 2-oxidoanilinium ylides (7) rearrange on heating to give the ethers (10) together with the dienones (8) and the phenols (11) for cases where the aromatic ring has a 5-alkyl substituent or a mixture of the dienones (8) and (12) for cases where the aromatic ring is 3,5-disubstituted. A study of the deuteriated ylides (25) shows that these reactions involve competing concerted and radical-pair processes. The base-catalysed rearrangements of the 2-hydroxy-N-pentadienylanilinium salts (33) give the ethers (34) and the phenols (35): these products result from competing concerted [1,4] and [5,4] rearrangements of the ylides (36) corresponding to the salts (33).

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Article information

DOI
https://doi.org/10.1039/P19810002930
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 2930-2942

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Base catalysed rearrangements involving ylide intermediates. Part 13. Further rearrangements of 2-oxidoanilinium ylides

W. D. Ollis, R. Somanathan and I. O. Sutherland, J. Chem. Soc., Perkin Trans. 1, 1981, 2930 DOI: 10.1039/P19810002930

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