28124-17-6

Upstream product

• 413615-58-4 (2,2-diphenylcyclopropyl)acetaldehyde 
• 75-11-6 diiodomethane 
• 7498-88-6 4,4-diphenylbut-3-enoic acid 
• 37555-48-9 2,2-diphenylcyclopropylmethanol 
• 59591-01-4 2,2-diphenylcyclopropanecarbaldehyde 
• 7150-12-1 2,2-diphenyl-cyclopropanecarboxylic acid 

Downstream Products

• 304867-63-8 (2,2-diphenylcyclopropyl)acetyl chloride 
• 936355-44-1 5-(2,2-diphenylcyclopropyl)pyrimidine-2,4(1H,3H)-dione 
• 936355-45-2 ethyl 2-(5-(2,2-diphenylcyclopropyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetate 
• 936355-46-3 ethyl 2-(5-(2,2-diphenylcyclopropyl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetate 
• 478814-62-9 2-(2,2-diphenylcyclopropyl)-1,1-diphenylethyl 4-nitrobenzenesulfenate 
• 490012-99-2 2-(2,2-diphenylcyclopropyl)-1,1-diphenylethanol 
• 478814-66-3 (C₆H₅)2C₃H₃C₂H₄OHC₆H₄C₆H₃ 
• 38674-44-1 methyl 2-(2,2-diphenylcyclopropyl)acetate 

Relevant academic research and scientific papers

Intermolecular enolate heterocoupling: Scope, mechanism, and application

This full account presents the background on, discovery of, and extensive insight that has been gained into the oxidative intermolecular coupling of two different carbonyl species. Optimization of this process has culminated in reliable and scalable proto

p-Nitrobenzenesulfenate esters as precursors for laser flash photolysis studies of alkyl radicals

A series of p-nitrobenzenesulfenate esters was used in laser flash photolysis (LFP) studies to generate alkoxyl radicals that fragmented to give the (2,2-diphenylcyclopropyl)methyl radical. Rate constants for the β-scission reactions increased as a function of the carbonyl compound produced in the fragmentation reaction in the order CH2O 2CO 2CO and increased with increasing solvent polarity. For alkoxyl radicals that fragment to produce benzaldehyde and benzophenone, the β-scission reactions are faster than 1,5-hydrogen atom abstractions when the incipient carbon radical is as stable as a secondary alkyl radical, and this entry to carbon radicals can be used in LFP kinetic studies.

Picosecond radical kinetics. Ring openings of phenyl substituted cyclopropylcarbinyl radicals

Rate constants for ring openings of the trans-(2-phenylcyclopropyl)carbinyl radical (1a), the cis-(2-phenylcyclopropyl)carbinyl radical (1b), and the (2,2-diphenylcyclopropyl)carbinyl radical (1c) were studied by competition kinetics using PTOC esters as radical precursors and hydrogen atom transfer trapping from benzeneselenol as the basis reaction. Radical la was studied in two solvents, toluene and THF; the experimental Arrhenius function for ring opening of 1a was log (kr·s) = 13.9 - 33/2.3RT (R in kcal/mol). It is possible that the immediate precursor to 1a, acyloxy radical 3a, suffers a concomitant decarboxylation-ring opening process that competes with simple decarboxylation leading to 1a. The experimental rate constant for ring opening of la at 25°C is 3 × 1011 s-1. Preliminary kinetic studies of radicals 1b and 1c gave Arrhenius functions of log (kr·s) = 13.9 - 3.1/2.3RT and log (kr·s) = 13.1 - 2.0/2.3RT, respectively, and the respective rate constants for ring openings at 25°C are 4 and 5 × 1011 s-1. Rate constants for ring openings of substituted cyclopropylcarbinyl radicals were estimated by Marcus theory using the known rate constants and equilibrium constant for the parent system and expected ΔG° values for the substituted systems. From these results, the estimated rate constants at 25°C for ring opening of 1a and 1b were 1 × 1011 s-1 and that for le was 4 × 1011 s-1. Precursors to radicals 1, such as the corresponding hydrocarbons, represent hypersensitive radical probes that, in principle, can provide unequivocal conclusions regarding the intermediacy of a radical in a reaction.