Abstract
The cyclization of (N,N-dimethylamino)[2-(prop-2-yn-1-yloxy)aryl]acetonitriles is carried out under phase-transfer conditions using powdered sodium hydroxide and benzyltriethylammoni- um chloride as catalyst in dimethyl sulfoxide to afford mixtures of a methylenechromane and a methylchromene via favored 6-exo-dig and 6-endo-dig processes, respectively. Several of the chromenes rearranged into benzofuranone derivatives during column chromatography on alumina and the formation of these is rationalized.
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