The Solvent Effect in the Rearrangement of 4- (N-Allyl-N-tosylamino) Naphthal-N-methylimide

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  • 4- (N-アリル-N-トシルアミノ) ナフタル酸-N-メチルイミドの転位における溶媒効果
  • 4- N-アリル-N-トシルアミノ ナフタルサン-N-メチルイミド ノ テンイ ニ オケル ヨウバイ コウカ
  • 本報を “アミドークライゼン転位反応に関する研究 (第2報)” とする

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The rates of rearrangement of 4- (N-allyl-N-tosylamino) naphthal-N-methylimide (1) at 205, 215 and 225°C in 9 solvents have been determined. The rearrangement was a first order reaction in every case and so insensitive to the nature of the solvent that the rates varied within only a 3.4-fold range. Hydroxylic solvents such as ethylene glycol and phenol were relatively useful for accellerating the reaction. The entropies of activation had negative values.<BR>These results show that the rearrangement proceeds via a transition state similar to that of the usual Claisen rearrangement.

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