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Base Catalysed Rearrangements involving Ylide Intermediates. Part 15. The Machanism of the Stevens Rearrangement

DOI: 10.1039/P19830001009

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1009 - 1027 (1983)

Update date:2022-08-05

Topics: Catalyst   Mechanism   Experimental   Base catalysed rearrangements   Ylide intermediates  

Authors:

Ollis, W. DavidOllis, W. David

Rey, MaxRey, Max

Sutherland, Ian O.Sutherland, Ian O.

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Article abstract of DOI:10.1039/P19830001009

The Stevens <1,2> rearrangement of acyl-stabilised ammonium ylides has been investigated with regard to stereoselectivity, intramolecularity and the formation of products in addition to the <1,2> rearrangement product.A detailed study of the effects of reaction conditions upon the rearrangement of the ylide derived from the salt (13) has shown that the stereoselectivity (retention of the configuration of the chiral migrating group) and intramolecularity decrease as solvent viscosity decreases.The rearrangement of the salt (13) in water at 0 deg C is essentially intramolecular with virtually complete retention of the configuration of the migrating group.These results, together with the isolation of products that can be rationalised on the basis of random free-radical coupling, indicate that the <1,2> rearrangement of acyl-stabilised ammonium ylides normally involves a radical pair mechanism.

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Product name:(R,S)-NN-dimethyl-N-phenacyl-1-p-nitrophenylethylammonium bromide

Cas No:87258-58-0

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