Australian Journal of Chemistry

The formation of 5, 6, 7, 8-Tetrahydronaphthalene-1, 3-dicarbonitrile by thermal rearrangement of Cyclohex-1-enyl (prop-2-ynyl) malononitrile

RFC Brown, CG McAllan

Index: Brown,R.F.C.; McAllan,C.G. Australian Journal of Chemistry, 1977 , vol. 30, p. 1747 - 1755

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Abstract

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 ...