Relative Reactivity of the Aromatic Ring in Benzo-1,3-dioxole, Its Cyclohomologues and Veratrole

Abstract

A study of the reactivities of benzo-1.3dioxole( I , n=l), benzo-1.4-dioxane(1, n=2), benzo-1.5-dioxepane(1, n .3 ) and veratrole (2) is of great interest, since those 1,2-dialkoxybenzenes are essential structural fragments of many natural and synthetic biologically active substances1.'and the synthesis of their derivatives often results in the formation of new compounds of practical interest.'However, many aspects of reactivity and other properties of compounds & and 2 have received insufficient study and the standpoints referred to in publications are of contradictory nature and need additional experimental verification.2-13 * Potential curve of methoxy-group rotation around the CAr-0 bond in veratrole ha8 no sharp energy minimums.