Divergent Reactivity of D-A Cyclopropanes under PTC Conditions, Ring-Opening vs. Decyanation Reaction

The divergent reactivity of D-A cyclopropane, under PTC conditions, is herein reported. Thus, a ring-opening or decyanation reaction can be achieved by reacting 2-arylcyclopropane-1,1-dicarbonitriles 1 with thioacetic acid in different conditions. use solid Cs2CO3 leads unexpectedly to the synthesis new cyclopropane derivatives via reaction, followed diastereoselective acetylation, whereas an aqueous solution results typical formation S-thiolate products. Therefore, tailored conditions allows one obtain either cyclic open-chain products moderate good yields.