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Note | Regular issue | Vol 51, No. 1, 1999, pp.169-177
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8347
Preparation and Hydrolysis of 3-Alkoxy-5-amino-4,6-dicyano-1,8,8-trimethyl-2-azabicyclo[2.2.2]octa-2,5-dienes

Yoshiharu Nakano,* Yoshitaka Kaneko, and Wu Ai Fen

*Faculty of Science, Ibaraki University, 2-1-1 Bunkyo, Mito, Ibaraki 310-8512, Japan


Solid base catalyzed condensation reaction of acetone with malononitrile in alcohol gave 3-alkoxy-5-amino-4,6-dicyano-1,8,8-trimethyl-2-azabicyclo[2.2.2]octa-2,5-dienes. The 2-aza bridge of the compound was cleaved hydrolytically in dilute hydrochloric acid to give 6-carbomethoxy-2,6-dicyano-3,5,5-trimethylcyclohex-2-enone. The compound was further decarbomethoxylated in this conditions to give 2,6-dicyano-3,5,5-trimethylcyclohex-2-enone of which crystal structure was determined by X-Ray diffraction method.