
%0 Journal Article
%A Brown, RFC 
%A McAllan, CG 
%T The formation of 5,6,7,8-Tetrahydronaphthalene-1,3-dicarbonitrile by thermal rearrangement of Cyclohex-1-enyl(prop-2-ynyl)malononitrile
%J Australian Journal of Chemistry
%D 1977/08/01
%V 30
%N 8
%P 1747-1755
%K 
%R https://doi.org/10.1071/CH9771747
%U https://www.publish.csiro.au/paper/CH9771747 
%X 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 dehydrogenation. An o-quinonoid imine (10) has been trapped with N- phenylmaleimide and other dienophiles. Dehydrogenation of the adduct (11) with Pd/C in boiling Ph2O proceeds with hydrogenolysis of a cyano group to a methyl group. 
