Use of the Vicinal Element Effect for Regiochemical Control of Quinone Substitutions and Its Implication for Convergent Mitomycin Construction
journal contributionposted on 23.10.2001, 00:00 by Amie L. Cox, Jeffrey N. Johnston
Nucleophilic substitution reactions of 2-methoxy-3-alkyl-p-benzoquinones are described as they relate to the construction of the mitomycin backbone. Normally controlled by activating groups attached to the olefin, the observed regioselection in these cases is determined by the deactivating substituent. Approximation of carbonyl activating ability would not have predicted the behavior of two systems investigated in which the poorer of two leaving groups is substituted in each case.