Synthesis and face-selective Diels-Alder reaction of homodehydroisodicyclopentadiene.
The title compd. (I) was prepd. from the mesylate II via ring cleavage, redn. to the alc., and dehydration. Tricyclo[6.2.1.02,6]undeca-2,6,9-triene was also prepd. from II. I underwent face-selective Diels-Alder reaction with non-acetylenic dienophiles, whereas reaction with acetylenic dienophiles gave a mixt. of adducts. Crystal structures are reported for 2 of the adducts.
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