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The triplex intramolecular Diels-Alder reaction of cyclopentadienes and styrene-like dienophiles that are linked with an alkyl chain was investigated. Sensitized irradiation of alkenylcyclopentadiene with 9,10-dicyanoanthracene leads to a [4 + 2] adduct without [1,5]-hydrogen shift when the linking chain contains three carbon atoms. If the linking chain contains only two carbon atoms, [1,5]-hydrogen...