111448-45-4

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 4606-07-9 ethyl cyclopropylcarboxylate 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 23719-80-4 cyclopropylmagnesium bromide 

Downstream Products

• 852822-63-0 tert-butyl cyclopropyl[bis(4-methoxyphenyl)]methyl peroxide 
• 111448-46-5 1-[4-bromo-1-(4-methoxyphenyl)but-1-en-1-yl]-4-methoxybenzene 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 7152-03-6 p-methoxyphenyl cyclopropyl ketone 
• 852822-70-9 cyclopropyl[bis(4-methoxyphenyl)]methoxyl radical 

Relevant academic research and scientific papers

Preparation of Functionalized Diaryl- and Diheteroaryllanthanum Reagents by Fast Halogen–Lanthanum Exchange

Aryl and heteroaryl halides (X=Br, I) undergo a fast and convenient halogen–lanthanum exchange with nBu2LaMe, which leads to functionalized diaryl- and diheteroaryllanthanum derivatives. Subsequent trapping reactions with selected electrophiles, such as ketones, aldehydes, or amides, proceeded smoothly at ?50 °C in THF, affording polyfunctionalized alcohols and carbonyl derivatives. Kinetic competition experiments revealed a similar reactivity trend as for Br/Mg exchange, but 106-times higher rates, making it comparable to Br/Li exchange.

A method for synthesis of homoallylic bromide

Cyclopropyl Grignard reagents react with carbonyl compounds in the presence of diethyl phosphite to give homoallylic bromides. The reaction is effectively carried out under mild conditions in a one-pot fashion with moderate to good yields.

Rapid access to halohydrofurans via bronsted acid-catalyzed hydroxylation/halocyclization of cyclopropyl methanols with water and electrophilic halides

A one-pot, two-step method to prepare 3-halohydrofurans efficiently by TfOH-catalyzed hydroxylation/halocyclization of cyclopropyl methanols with H2O and N-halosuccinimide (NXS, X=1, Br, Cl) or Selectfluor is described. The reactions proceed rapidly under mild and operationally straightforward conditions with a catalyst loading as low as 1 mol % and afford the 3-halohydrofuran products in moderate to excellent yields and, in most cases, with preferential cis diastereoselectivity. The method was shown to be applicable to cyclopropyl methanols containing electron-withdrawing, electron-donating, and sterically demanding functional groups and electrophilic halide sources. The mechanism is suggested to involve protonation of the alcohol substrate by the Bronsted acid catalyst and ionization of the starting material. This results in ring-opening of the cyclopropane moiety and in situ formation of a homoallylic alcohol intermediate, which undergoes subsequent intramolecular halocyclization on treating with the electrophilic halide source to give the halohydrofuran. The observed cis product selectivity is thought to be determined by the reaction proceeding through an in situ generated unsaturated alcohol intermediate that contains a (Z)-alkene moiety under the kinetically controlled conditions.

The effect of ring substitution on the O-neophyl rearrangement of 1,1-diarylalkoxyl radicals. A product and time-resolved kinetic study

A product and time-resolved kinetic study of the effect of ring substitution on the reactivity of 1,1-diarylalkoxyl radicals has been carried out. The radicals undergo an O-neophyl shift to give the isomeric 1-aryl-1-aryloxyalkyl radicals from which the corresponding aromatic ketones are formed. The rearrangement rate constants are influenced by ring substitution, increasing in the presence of electron-withdrawing substituents and decreasing in the presence of electron-donating ones. From the results of product and kinetic studies, the following migratory aptitudes have been obtained: 4-trifluoromethylphenyl > phenyl ? 4-methylphenyl > 4-methoxyphenyl. Excellent Hammett-type correlations between the σ+ substituent constants and both the visible absorption band maxima and the rearrangement rate constants have been obtained. The experimental results indicate that the rearrangement is governed by electronic effects in the starting 1,1-diarylalkoxyl radicals, whereas the stability of the rearranged carbon-centered radical plays a minor role, in line with a reactant-like transition state, strongly supporting the hypothesis that the O-neophyl rearrangement of 1,1-diarylalkoxyl radicals proceeds through a concerted mechanism.

Diarylalkyl-substituted alkylamines and medicaments containing them

A compound I STR1 in which R1 is cycloalkyl, alkenyl, cycloalkenyl, phenyl, STR2 where J, L, M, and E are methine or nitrogen and J', L', M', and E' are methylene, carbonyl or imino; R2 is phenyl or phenylalkyl; a is various amine ra