Reaction of DL-trans-and DL-cis-2-Halo-1-benzenesulfonamidocyclohexanes. Formation and the Reaction of N-Benzenesulfonylcyclohexenimine.

Abstract

DL-trans-2-Halo-1-benzenesulfonamidocyclohexane (II) reacted with base such as silver acetate in benzene, cold sodium ethoxide, or cold ethanolic potassium hydroxide affording meso-cis-N-benzenesulfonylcyclohexenimine (I). The ring opening of I occurred by the action of hot ethanolic potassium hydroxide, hot sodium ethoxide, sodium hydrosulfide, acetic acid or hydrogen halides to form 2-substituted trans-1-benzenesulfonamidocyclohexanes (III, V, VI, IV, and II, respectively). Action of silver acetate on II in acetic acid afforded IV. Contrary to the reactions of II, the cis isomer (VII) did not form an imine ring. An equilibrium was effected between I and II in the presence of a small amount of alkali, and heating of I with excess of mineral salts such as potassium halide and sodium halide, gave II.