156ChemInform Abstract 2,3-Dicyanonorbornadiene (I) reacts with the dienes (II) or (VI), producing the adducts (III) or (VII) which are hydrogenated to give (IV) or (VIII). Decyanation with Na/THF yields the olefins (V) or (IX). The isomeric dinitriles (X) react with (VIa), forming the nitriles (XI) after hydrogenation. These are decyanated to produce 1,2-dicyanonorbornene (XII). Reaction of (XII) with the dienes (II) or (VI) gives the adducts (XIII) and (XIV) respectively and these are hydrogenated, yielding (IV) and (VIII). The dienes (XV) and (XVI) are prepared from (XIII) or (XIVb) by decyanation. The compounds (XV) and (XVI) are transformed into benzonorbornene (XVIII) by oxidation with air or pyrolysis.
Diels‐Alder reaction of the dicyano compound (I) with the diene (II) yields the exo product (III) (space group P212121 with Z=4), which is transformed to the title compound (V).
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