Unusual mechanism of hydrolysis of the tosyl cyanide–cyclopentadiene adduct to the lactam 2-azabicyclo [2.2. 1] hept-5-en-3-one

PE Morgan, R McCague, A Whiting

Index: Morgan, Paul E.; McCague, Ray; Whiting, Andrew Chemical Communications, 1996 , # 15 p. 1811 - 1812

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Citation Number: 2

Abstract

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.