182740-91-6

Basic information

• Product Name: dibenzyl-2-vinylcyclopropane-1,1-dicarboxylate
• Synonyms: dibenzyl-2-vinylcyclopropane-1,1-dicarboxylate
• CAS NO: 182740-91-6
• Molecular Weight: 336.387
• Mol File: 182740-91-6.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: dibenzyl-2-vinylcyclopropane-1,1-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dibenzyl-2-vinylcyclopropane-1,1-dicarboxylate(182740-91-6)
• EPA Substance Registry System: dibenzyl-2-vinylcyclopropane-1,1-dicarboxylate(182740-91-6)

Safety Data

• Hazardous Substances Data: 182740-91-6(Hazardous Substances Data)

Upstream product

• 821-06-7 (E)-1,4-dibromobutene 
• 15014-25-2 malonic acid dibenzyl ester 
• 1774-47-6 trimethylsulfoxonium iodide 
• 6974-12-5 1,4-dibromo-2-butene 
• 10463-48-6 3,4-dibromo-1-butene 

Relevant articles and documents

Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex

We report the development of a new aminoxyl radical catalyst, CHAMPO, for the electrochemical diazidation of alkenes. Mediated by an anodically generated charge-transfer complex in the form of CHAMPO-N3, radical diazidation was achieved across a broad scope of alkenes without the need for a transition metal catalyst or a chemical oxidant. Mechanistic data support a dual catalytic role for the aminoxyl serving as both a single-electron oxidant and a radical group transfer agent.

Photoredox catalysed allylic trifluoromethylation via ring opening of vinyl cyclopropanes using Langlois reagent

Trifluoromethylation of vinylcyclopropanes (VCPs) has been developed under mild reaction conditions to synthesize allylic trifluoromethylated derivatives with high yield and E/Z selectivity using visible light photo-redox catalysis and Langlois reagent (CF3SO2Na) as a trifluoromethylation source. Further, we demonstrate a gram scale synthesis procedure for a trifluoromethylation of vinylcyclopropane.

Pd-Catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with 2-Vinylcyclopropane-1,1-dicarboxylates

A trans-diastereoselective Pd-catalyzed dearomative [3 + 2] cycloaddition between vinylcyclopropane dicarboxylates and 3-nitroindoles has been developed. The reaction provides densely functionalized cyclopenta[b]indolines with versatile vinyl and nitro-groups. The addition of a halide additive was found to be critical for the diastereoselectivity of the reaction, which is proposed to be a result of a rapid π-σ-π interconversion between the intermediates allowing for Curtin-Hammett control. A switch in diastereoselectivity to afford products with the vinyl and nitro groups cis to each other is observed with a 4-substituted 3-nitroindole.