The intramolecular photocycloaddition of a 1-cyanonaphthalene derivative in microreactors made of poly(dimethylsiloxane) (PDMS) was examined. By using the microreactors and flow system, both the efficiency and regioselectivity increased compared with those under batch conditions.

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Intramolecular [2+2] and [2+3] photocycloadditions of 2-(2-alkenyloxymethyl)naphthalene-1-carbonitriles and their photocycloreversion using glass-made microreactors were investigated in comparison with photoreactions under conventional batch conditions. Both the efficiency and regioselectivity were improved by use of glass-made microreactors. These results can be explained by thorough absorption of light and outflow of primary product from the reaction system.

Rings from light: Irradiation of acetonitrile solutions containing 1‐cyano‐2‐(4‐pentenyl)naphthalene derivatives afforded benzotetra‐ and benzopentacyclic compounds with tri‐ and tetraquinane skeletons in high yields, through intramolecular [2+3] photocycloaddition of the alkene at the 2,4‐positions of the cyanonaphthalene (see scheme; n=1, 2). The structures of these adducts were confirmed by their spectral properties and by X‐ray crystallographic analyses.

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