论文信息 - Unusual mechanism of hydrolysis of the tosyl cyanide–cyclopentadiene adduct to the lactam 2-azabicyclo[2.2.1]hept-5-en-3-one

Unusual mechanism of hydrolysis of the tosyl cyanide–cyclopentadiene adduct to the lactam 2-azabicyclo[2.2.1]hept-5-en-3-one

Hydrolysis of the cycloaddition product derived from tosyl cyanide and cyclopentadiene was investigated using 18O label incorporation experiments; thus, sulfonyl imine 2 was transformed into 18O labelled lactam 3 with 18O labelled acetic acid, which is consistent with the intervention of intermediate 6 during the hydrolysis.

A. Whiting | R. Mccague | P. Morgan

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