61692-96-4

Upstream product

• 143959-06-2 ethyl N-nitroso-N-<(E)-2-(p-chlorophenyl)-3-phenylcyclopropyl>carbamate 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 622-95-7 4-chlorobenzyl bromide 
• 1009080-82-3 ((S)-1-((S)-1-(4-chlorophenyl)-3-phenylprop-2-yn-1-yl)pyrrolidin-2-yl)methanol 
• 104-88-1 4-chlorobenzaldehyde 
• 19277-54-4 p-chlorophenyldiazomethane 
• 536-74-3 phenylacetylene 
• 52372-80-2 (4-chlorobenzylidene)hydrazine 
• 143958-97-8 ethyl N-<(E)-2-(p-chlorophenyl)-3-phenylcyclopropyl>carbamate 
• 32096-16-5 (E)-2-(p-chlorophenyl)-3-phenylcyclopropanecarboxylic acid 
• 1657-50-7 (E)-1-(4-chlorophenyl)-2-phenylethene 
• 61692-86-2 1-chloro-4-(3-phenylprop-2-yn-1-yl)benzene 
• 6738-06-3 phenylethynylmagnesium bromide 
• 1530-39-8 (4-chlorobenzyl)triphenylphosphonium chloride 

Relevant academic research and scientific papers

A Versatile Room-Temperature Route to Di- and Trisubstituted Allenes Using Flow-Generated Diazo Compounds

A copper-catalyzed coupling reaction between flow-generated unstabilized diazo compounds and terminal alkynes provides di- and trisubstituted allenes. This extremely mild and rapid transformation is highly tolerant of several functional groups. Well tolerated: A mild copper-catalyzed coupling reaction between unstabilized diazo compounds (generated in flow) and terminal alkynes is reported. The method provides di- and trisubstituted allenes with high functional-group tolerance.

Silver(i)-mediated highly enantioselective synthesis of axially chiral allenes under thermal and microwave-assisted conditions

Silver(i) salts mediated stereospecific transformation of optically active propargylamines to axially chiral allenes with excellent enantioselectivities (17 examples with 96-99% ee; one substrate with 91% ee) without subsequent racemization.

Gold-catalyzed highly enantioselective synthesis of axially chiral allenes

Axially chiral allenes are synthesized from chiral propargylamines catalyzed by KAuCl4 in high yields (up to 93% yield) and excellent enantioselectivities (up to 97% ee) in CH3CN at 40 °C. The reaction has been applied to the synthes

Electron Demand in the Transition State of the Cyclopropylidene to Allene Ring Opening

The electronic structure of the transition state for the cyclopropylidene to allene conversion has been probed.The methodology involved the relative rates of ring opening vs trapping by MeOH for a series of variously substituted 2,3-diarylcyclopropylidenes.With the assumption that the rate of trapping was unaffected by substituents, a Hammett correlation was constructed.The negative value (-0.72) for ρ indicated that the carbenic center attracts electron density in the ring-opening transition state, much like the cyclopropyl cation to allyl cation transition state.Temperature-dependent studies showed that the observed preference for ring opening was driven by entropy factors.Also, using reasonable estimates for the close to diffusion-controlled trapping activation enthalpies, the derived enthalpies for ring opening were in close agreement with the best theoretical values.