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Rearrangement During Recrystallisation

Condensation of the pyrrolidine enamine of cyclohexanone with l,l-dicyano-2,2-dimethylcyclopropane proceeds smoothly in refluxing dry xylene and gives the expected adduct in 76% yield. Recrystallisation of the adduct from 95% ethanol, however, gave a 91% yield of a product which no longer contained the pyrrolidine group but whose spectral data clearly showed the presence of a ketone group and an enaminonitrile function. Hydrolysis of this latter product with phosphoric acid/acetic acid gave 5-(2-oxo-4,4-dimethylcyclopentyl)pentanoic acid in 83% yield. [Pg.104]

Elucidate the reaction sequence and give mechanisms for the transformations. [Pg.104]


See other pages where Rearrangement During Recrystallisation is mentioned: [Pg.104]    [Pg.104]    [Pg.1268]    [Pg.1297]    [Pg.180]    [Pg.67]   


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Recrystallisation

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