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We know of several limitations of the Rh2TPA 4-catalyzed cyclopropanation reaction. Unlike the analogous reactions of ethyl α-diazopropionate to give 8f and 8g, the reactions of ethyl α-diazobutanoate (1 equiv) with either 1,1-diphenylethylene (3 equiv) or 1-vinylmesitylene (3 equiv) were both unsuccessful, and led predominantly to β-hydride elimination. Cyclopropane products were not observed in the reactions of ethyl α-diazobutanoate with 1-vinylcyclohexane, trans-β-methylstyrene, cis- diphenylethylene, or 1-octene. The reaction of ethyl α- diazohydrocinnamate (3 equiv) with styrene proceeded with poor efficiency: in hexane, the cyclopropanation product was formed in 28% yield (NMR analysis) along with uncharacterized products and unreacted styrene
-
4-catalyzed cyclopropanation reaction. Unlike the analogous reactions of ethyl α-diazopropionate to give 8f and 8g, the reactions of ethyl α-diazobutanoate (1 equiv) with either 1,1-diphenylethylene (3 equiv) or 1-vinylmesitylene (3 equiv) were both unsuccessful, and led predominantly to β-hydride elimination. Cyclopropane products were not observed in the reactions of ethyl α-diazobutanoate with 1-vinylcyclohexane, trans-β-methylstyrene, cis- diphenylethylene, or 1-octene. The reaction of ethyl α- diazohydrocinnamate (3 equiv) with styrene proceeded with poor efficiency: in hexane, the cyclopropanation product was formed in 28% yield (NMR analysis) along with uncharacterized products and unreacted styrene.
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