24959-22-6

Upstream product

• 2648-61-5 2,2-dichloroacetophenone 
• 2700-22-3 Benzylidenemalononitrile 
• 24959-22-6 (±)-2-benzoyl-3-phenylcyclopropane-1,1-dicarbonitrile 
• 16883-69-5 N-phenacylpyridinium bromide 
• 1885-22-9 bromomalononitrile 
• 94-41-7 benzalacetophenone 
• 94360-09-5 3-benzoyl-1-bromo-2-phenyl-1,1-dicyanopropane 
• 70-11-1 α-bromoacetophenone 
• 109-77-3 malononitrile 
• 62940-90-3 2-(3-oxo-1,3-diphenylpropyl)malononitrile 

Downstream Products

• 104230-12-8 trans-1,1-dicyano-4-phenoxy-4-phenylbuta-1,3-diene 
• 104230-11-7 cis-1,1-dicyano-4-phenoxy-4-phenylbuta-1,3-diene 
• 24959-22-6 cis-2-phenyl-3-benzoyl-1,1-cyclopropanedicarbonitrile 
• 1145-01-3 3,5-Diphenylpyrazole 
• 56162-63-1 2-oxo-6-phenyl-1,2-dihydropyridine-3-carboxylic acid 

Relevant academic research and scientific papers

Hypoiodite-mediated catalytic cyclopropanation of alkenes with malononitrile

An efficient synthetic procedure for di-cyano-cyclopropanation of alkenes using catalytic amounts of molecular iodine as a precatalyst and tert-butyl hydroperoxide (TBHP) as a terminal oxidant under mild conditions has been developed. This catalytic reaction works especially well for the aryl-substituted double bond affording products of cyclopropanation in high yields. A catalytic cycle based on the generated in situ hypoiodite species has been proposed,.

Indium(I) bromide-promoted stereoselective preparation of cyclopropanes via sequential aldol-type coupling/elimination/Michael-induced ring closure reaction from α,α-dichloroacetophenone and aldehydes

The indium enolate generated from indium(I) bromide and α,α-dichloroacetophenone reacts with aldehydes to produce (syn + anti)-2-chloro-3-hydroxy-propan-1-ones which can be converted to their trans-prop-2-en-1-ones derivatives upon reaction with an extra equivalent of InBr. The enones undergo Michael-induced ring closure reactions with an extra equivalent of the initial enolate to afford the corresponding cyclopropane derivatives, according to a sequenced reaction mechanism.

One-pot method for stereoselective cyclopropanation of electron-deficient olefins with methyl bromoacetate and phenacyl bromide in the presence of triphenylarsine

A triphenylarsine-catalyzed one-pot procedure for the preparation of cis-cyclopropanes with acyclic electron-deficient olefins with carbonyl-stabilized arsonium ylides formed from methyl bromoacetate or phenacyl bromide in the presence of NaHCO3/sub

AN UNUSUAL PHOTOCHEMICAL REARRANGEMENT; MECHANISTIC AND EXPLORATORY ORGANIC PHOTOCHEMISTRY

An unusual rearrangement of 1-benzoyl-2,2-dicyano-3-phenylcyclopropane is described and compared with the photochemistry of 1-benzoyl-2-phenylcyclopropane.Evidence is advanced for facile fission of the three-ring bond bearing benzoyl and cyano substituents.

CYCLIZATION OF NITRILES. IX. SYNTHESES BASED ON 2-ARYL-3-AROYL-1,1-DICYANOPROPANES

2-Aryl-3-aroyl-1,1-dicyanopropanes and 2-aryl-3-aroyl-1-bromo-1,1-dicyanopropanes were synthesized from chalcones and malononitrile and were converted into 4,6-diaryl-2-bromo-3-cyanopyridines and 3-cyano-2(1H)-pyridinethiones.The 2-aryl-3-aroyl-1-bromo-1,1-dicyanopropanes proved convenient intermediates for the production of the corresponding cyclopropanes and other compounds.By their reaction with urea a new method was developed for the production of substituted 3-cyano-2(1H)-pyridinethiones.The 2-bromo-3-cyanopyridines contain a mobile bromine atom readily exchanged for the various nucleophilic residues of alcohols and amines and for iodide, and cyano and thiocyanato groups.The 3-cyano-2(1H)-pyridinethiones were used in the synthesis of 3-aminothienopyridines through the isolated 2-Z-methylthio-3-cyanopyridines.