59117-58-7

Upstream product

• 67-56-1 methanol 
• 4030-17-5 4-methoxyphenylcyclopropane 
• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 
• 74-88-4 methyl iodide 
• 15823-04-8 methyl 3-(4-methoxyphenyl)propionate 
• 10210-17-0 3-(4-hydroxyphenyl)propan-1-ol 
• 616-38-6 carbonic acid dimethyl ester 
• 61542-10-7 1-iodo-3-methoxypropane 
• 696-62-8 para-iodoanisole 

Relevant academic research and scientific papers

Single-Electron-Transfer-Induced Coupling of Alkylzinc Reagents with Aryl Iodides

Alkylzinc reagents prepared from an alkyllithium and zinc iodide were found to undergo coupling with aryl and alkenyl iodides in the presence of LiI in a mixed solvent consisting of THF and diglyme (1:1). Alkyllithiums, prepared by halogen–lithium exchange between an alkyl iodide and tert-butyllithium, are also converted to alkylarenes through alkylzinc reagents.

Reactions of p-coumaryl alcohol model compounds with dimethyl carbonate. Towards the upgrading of lignin building blocks

Cinnamyl alcohol 1 and 4-(3-hydroxypropyl)phenol 2, two compounds resembling the lignin building block p-coumaryl alcohol, can be selectively transformed into different products by catalytic methodologies based on dimethyl carbonate (DMC) as a green solvent/reagent. Selectivity can be tuned as a function of the reaction temperature and of the nature of the catalyst. Basic catalysts such as K2CO3, trioctylmethylphosphonium methylcarbonate ([P8881][CH3OCOO]), and CsF/αAl 2O3 promote selective transesterification of the aliphatic hydroxyl group at 90 °C. However, amphoteric solids such as alkali metal-exchanged faujasites, NaX and NaY, selectively yield the corresponding alkyl ethers at higher temperatures (165-180 °C). The phenolic hydroxyl group of 2 can be methylated similarly with the faujasites at high temperatures. This preliminary screening for selectivity illustrates reactivity trends and delineates some of what might be among the most promising synthetic pathways to upgrade lignin-derived chemical building blocks.

Reduction of carboxylic esters to ethers with triethyl silane in the combined use of titanium tetrachloride and trimethylsilyl trifluoromethanesulfonate

Aliphatic acyclic and cyclic ethers are prepared on treatment of their corresponding carboxylic esters and lactones with triethylsilane in the presence of titanium tetrachloride and trimethylsilyl trifluoromethanesulfonate.

Oxygen versus carbon acidity in the side-chain fragmentation of 2-, 3-, and 4-arylalkanol radical cations in aqueous solution: The influence of the distance between the OH group and the aromatic ring

The decay of 2-, 3-, and 4-(4-methoxyphenyl) alkanol radical cations in water has been kinetically investigated by pulse radiolysis, the reaction products being determined either by steady-state γ-radiolysis experiments or by reactions promoted by potassium 12-tungstocobalt(III)ate, a bona fide one-electron oxidant. It was found that all 2-arylalkanol radical cations react with -OH at a diffusion-controlled rate leading to Cα-Cβ bond cleavage products. This suggests a reaction induced by deprotonation at the alcoholic OH group. In acidic medium (pH = 4), the rates of decay of these radical cations are much lower leading to Cα-H deprotonation (for 2-(4-methoxyphenyl)ethanol (1.+) and 1-(4-methoxyphenyl)-2-propanol (4.+)) or Cα-Cβ bond cleavage products (for 1-phenyl-2-(4-methoxyphenyl)ethanol (5.+) and 2-methyl-1-phenyl-3-(4-methoxyphenyl)-2-propanol (6.+)). The 3-(4-methoxyphenyl)propanol radical cation (2.+) reacts in acidic medium (pH = 4) at a rate close to that of 1.+, undergoing Cα-H deprotonation. In contrast, in basic medium (pH = 10) 2.+ produces 3-(4-methoxyphenyl)propanal, with a rate ～5-fold lower than that of 1.+, again indicating a reaction promoted by O - H deprotonation. With 4-(4-methoxyphenyl)-1-butanol radical cation (3.+), products of Cα - H deprotonation were observed both in the presence and in the absence of -OH. These results are discussed in terms of a mechanistic dichotomy, that is, carbon versus oxygen acidity, which appears to be operating for 2-and 3-arylalkanols whereas with 4-arylalkanol radical cations only carbon acidity is observed.

PHOTOINDUCED OXIDATIVE CLEAVAGE OF ARYLCYCLOPROPANES IN THE PRESENCE OF ORGANIC ELECTRON-ACCEPTOR

The cyclopropane ring of arylcyclopropanes is oxidatively cleaved by irradiation in polar solvents containing nucleophiles such as alcohols, water, and sodium cyanide in the presence of electron-acceptor such as 1,4-dicyanobenzene and 1-cyanonaphthalene, giving nucleophile-incorporated products.This photoreaction proceeds via an electron-transfer from the cyclopropanes to the excited electron-acceptors, and the cation radicals of arylcyclopropanes are involved as key intermediates.