Reactions of Carbonyl Compounds in Basic Solutions. Part 27.1 Alkaline Hydrolysis of Bridged Benz[de]isoquinolin-1-ones: Torsionally Distorted Lactams

Abstract

Rate coefficients have been measured for the alkaline hydrolysis of 2,3-ethanoxy- and 2,3-propanamino-2,3-dihydro-1H-benz[de]isoquino lin-1-ones‡ in 70% (v/v) dimethyl sulfoxide–water at several temperatures and of N,N-dimethyl-1-naphthamide in water: the relative rates of hydrolysis, activation parameters and other studies indicate the importance of the torsional distortion of the lactam nitrogen and steric $lsquo;bulk’ factors in controlling reactivity.