82217-68-3Relevant academic research and scientific papers
Base Catalysed Rearrangements involving Ylide Intermediates. Part 14. Rearrangements of 4-Oxidoanilinium Ylides and 3-Oxidoanilinium Betaines
Mageswaran, Sivapathasuntharam,Ollis, W. David,Somanathan, Ratnasamy,Sutherland, Ian O.
, p. 893 - 902 (2007/10/02)
The N-allyl-4-oxidoanilinium ylides (11a-c) undergo a sigmatropic rearrangement at 0 deg C to give initially the products (9a-c), which undergo a further rearrangement to give the isolated reaction products (8a-c).The N-(3,3-dimethylallyl)-4-oxidoanilinium ylide (11d) reacts at 0 deg C by the alternative pathway involving homolysis and radical pair recombination to give a mixture of the products (8d) and (13d).The ylides (15a-c) rearrange by a similar radical pair mechanism.The N-pentadienyl-4-oxidoanilinium ylides derived from the salts (24a and b) also rearrange at 0 deg C by a sequence of and sigmatropic rearrangements to give in each case the product (26b).The N-allyl-3-oxidoanilinium betaines (29a and b) undergo rearrangements on heating at 40 deg C to give mixtures of the products (32) and (33) whereas the N-pentadienyl-3-oxidoanilinium ylide (30) gives only the product (35) of a rearrangement followed by aromatisation.
