Ju-Yeon Lee, H. Hall
Mar 1, 1990
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Abstract
Abstract : One,1-Dimethoxy-2-bromoethylene 1 reacts with tetracyanoethylene (TCNE,3) at -10 C to form methyl 2,2,3,3-tetracyanocyclopropanecarboxylate 6 in high yield. A similar reaction occurs with 1,1-diethoxy-2-bromoethylene 2 to yield ethyl 2,2,3,3-tetracyanocyclopropanecarboxylate 7. Further, Beta-bromoethyl 2,2,3,3-tetracyano-1-methylcyclopropanecarboxylate 10 and Beta-bromoethyl 2,2,3,3-tetracyano-1-ethylcyclopropanecarboxylate 11 were obtained by reacting TCNE with 2-bromomethylidene 8 and 2-bromoethylidene-1, 3-dioxolane 9, respectively. A reaction mechanism via a zwitterion and intra-molecular displacement of bromide is proposed.