Abstract Cyclohex-1-enyl (prop-2-ynyl) malononitrile (1), heated neat at 200, forms 5, 6, 7, 8- tetrahydronaphthalene-1, 3-dicarbonitrile (2) and much polymer. Two probable intermediates (4) and (5) have been isolated from rearrangements at lower temperatures and in hydrocarbon solvents. A reaction pathway is proposed which includes Cope rearrangement, apparent [1, 3] H shift, electrocyclic reaction,[1, 5] CN shift, and ...
