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Cyanomethylbenzaldehyde reacts in the presence of concentrated aqueous solution of sodium hydroxide or powdered potassium carbonate and a quaternary ammonium salt as a catalyst in benzene (phase-transfer catalysis) with 2-chloroethyl aryl ketones or electrophilic alkenes affording 1-cyano-3-acylnaphthalenes, 1-(2-cyano)- and 1-(2-phenylsulfonyl)ethyl-3-substituted naphthalenes or 1-cyano-5,8-diaroyl-benzobicyclo(2.2.2)octenes. Further cyclization of the corresponding 5,8-diacetyl derivative of 1-cyanobenzobicyclooctene gives 1-cyano-10- methyltetracyclo(7.5.1.0 2,7 .0 8,13 )pentadeca-2,4,6,10-tetraen-12-one. Formation of these products is rationalized.

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2-Cyanomethylbenzaldehyde – useful substrate for preparation of some 1,3-di- and 1,2,3-trisubstituted naphthalenes or substituted 1-cyanobenzobicyclo[2.2.2]octenes