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2-(Cycloamino)propenenitriles H2C=C(CN)N(CH2)n (n = 4, 5, 6, 7) are added to triplet ,*excited 1-acetonaphthone forming 8b-acetyl-2-(cycloamino)-1,2,2a,8b-tetrahydrocyclobuta[a]naphthalene-2-carbonitriles as well as 1-acetyl-9-(cycloamino)-1,4-dihydro-1,4-ethanonaphthalene-9-carbonitriles. Regioand stereoselectivity of the photocycloadditions and the special role of the cyclobuta[a]naphthalene adducts in the initial stage of the photoadditions are discussed.

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone