Issue 15, 1996

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

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.

Article information

Article type
Paper

Chem. Commun., 1996, 1811-1812

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

P. E. Morgan, R. McCague and A. Whiting, Chem. Commun., 1996, 1811 DOI: 10.1039/CC9960001811

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