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Paper | Regular issue | Vol 32, No. 10, 1991, pp.1989-2004
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5848
Diels-Alder Reaction of Photoenol of 2-Methylbenzaldehyde with 5-Alkyldene-1,3-dioxane-4,6-dione Derivatives

Takashi Tsuno and Kunio Sugiyama*

*Department of Industrial Chemistry, College of Industrial Technology, Nihon University, 1-2-1, Izumi-cho, Narashino, Chiba 275-8575, Japan


Spiro- and polyspirocyclic compounds containing the 1,2,3,4-tetrahydro-1-naphthol structure were obtained by the Diels-Alder reaction of the photoenol of 2-methylbenzaldehyde with 5-alkylidene-1,3-dioxane-4,6-dione derivatives. The cycloaddition proceeded regio- and stereoselectively. However, in the case using 5-benzylidene-2,2-dimethyl-1,3-dioxane-4,6-dione and diethyl isobutylidenemalonate, the cycloaddition failed.