
TY  - JOUR
A1  - Brown, RFC 
A1  - McAllan, CG 
T1  - The formation of 5,6,7,8-Tetrahydronaphthalene-1,3-dicarbonitrile by thermal rearrangement of Cyclohex-1-enyl(prop-2-ynyl)malononitrile
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1977
VL  - 30
IS  - 8
SP  - 1747
EP  - 1755
KW  - 
UR  - https://doi.org/10.1071/CH9771747 
N2  - 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. 
ER  -

