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Published on: April 4, 2014
Dimerization/Elimination of β-Styrylmalonates under Action of TiCl4
D D Borisov1, G R Chermashentsev1, K V Potapov1
1N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russia.
Abstract:
A new type of dimerization of dimethyl (β-styryl)malonates in the presence of TiCl4 accompanied by elimination of a methanol molecule was discovered. Selective methods for the synthesis of substituted trimethyl 4-hydroxy-[1,1'-biaryl]-3,3,5(2H)-tricarboxylates and trimethyl 7-hydroxy-9,10-dihydro-5,9-methanobenzo[8]annulene-6,8,8(5H)-tricarboxylates were developed. The regularities of the occurring processes were determined and a similar reaction of β-styrylmalonate with benzylidenemalonate in the presence of TiCl4 was performed in the scope of the suggested mechanism.
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