A Hammett correlation for CC-1065 and duocarmycin analogs: Magnitude of substituent electronic effects on functional reactivity

A quantitative Hammett study of the magnitude of the electronic effects of a C7 substituent on the functional reactivity of N-BOC-CBI (5, R=H), its impact on biological properties, details of the mechanism of the acid-catalyzed nucleophilic addition to the activated cyclopropane, and its implications on the origin of the DNA alkylation selectivity of this class of agents is detailed.