Journal of the Chemical Society. Perkin transactions I p. 2930 - 2942 (1981)
Update date:2022-08-05
Topics:
Ollis, W. David
Somanathan, Ratnasamy
Sutherland, Ian O.
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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