High stereoselectivity in the Diels-Alder reaction of substituted anthracenes: Reactions of 1-succinimidoanthracene and 1-phthalimidoanthracene with maleic anhydride

Abstract

1-Succinimidoanthracene undergoes Diels-Alder reaction with maleic anhydride to give mainly the <i style="">anti</i> adduct suggesting that the steric factors play dominant role in deciding the <i style="">anti/syn</i> stereoselectivity. 1-phthalimidoanthracene and also gives mainly the <i style="">anti</i> adduct with maleic anhydride. The configurations of the compounds have been established by preparing the corresponding imide derivatives of the anhydride adducts and observing the interactions between the imide substituent and the 1-substituent.The interactions between the 1-substituent and that on the anhydride ring of the adduct are more or less negligible in the <i style="">anti</i>-adduct.