Synthesis of prazolinones from β-N,N-dimethylhydrazinopropenoates: an example of a thermally induced [1,4] alkyl shift

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Abstract
Gas phase thermolysis of β-N,N-dimethylhdrazinopropenoates (1) provides a new route to pyrazolinones (2) involving a [1,4] methyl shift from nitorgen to carbon in the pyrazolinium ylide intermediates (3); the mechanism is supported by the isolation of ylides (3a,b,e), the structures of (3a) and (3e) being confirmed by X-ray crystallography.

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