2211-92-9

Usage

Compound type

Sulfoxide

Usage

Chiral auxiliary in organic synthesis

Specific application

Asymmetric synthesis reactions

Role

Chiral ligand in metal-catalyzed reactions

Benefits

Ability to form stable and selectively reactive complexes with various metal ions

Applications

Preparation of pharmaceuticals, agrochemicals, fine chemicals, and specialty materials

Importance

Unique structure and reactivity, valuable tool in the development of new synthetic methodologies, and the production of optically pure compounds.

Upstream product

• 107-47-1 sulfure de di tert-butyle 
• 7175-54-4 cumyl peroxy radical 

Downstream Products

• 64818-61-7 (tert-butylsulfinyl)cyclohexane 
• 107-47-1 sulfure de di tert-butyle 
• 4719-19-1 2-methyl-2-propanesulfenic acid 
• 75-66-1 2-methylpropan-2-thiol 
• 62076-10-2 (tert-butylsulfinyl)benzene 
• 133497-27-5 (±)-2-methyl-N-phenylpropane-2-sulfinamide 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 143028-36-8 4,4'-sulfinylbis((trifluoromethyl)benzene) 
• 50986-93-1 1-(phenylsulfinyl)-4-(trifluoromethyl)benzene 

Relevant academic research and scientific papers

Mechanisms of hydrogen-, oxygen-, and electron-transfer reactions of cumylperoxyl radical

Rates of hydrogen-transfer reactions from a series of para-substituted N,N-dimethylanilines to cumylperoxyl radical and oxygen-transfer reactions from cumylperoxyl radical to a series of sulfides and phosphines have been determined in propionitrile (EtCN) and pentane at low temperatures by use of ESR. The observed rate constants exhibit first-order and second-order dependence with respect to concentrations of N,N-dimethylanilines. This indicates that the hydrogen- and oxygen-transfer reactions proceed via 1:1 charge-transfer (CT) complexes formed between the substrates and cumylperoxyl radical. The primary kinetic isotope effects are determined by comparing the rates of N,N-dimethylanilines and the corresponding N,N-bis(trideuteriomethyl)anilines. The isotope effect profiles are quite different from those reported for the P-450 model oxidation of the same series of substrates. Rates of electron-transfer reactions from ferrocene derivatives to cumylperoxyl radical have also been determined by use of ESR. The catalytic effects of Sc(OTf)3 (OTf = triflate) on the electron-transfer reactions are compared with those of Sc(OTf)3 on the hydrogen- and oxygen-transfer reactions. Such comparison provides strong evidence that the hydrogen- and oxygen- transfer reactions of cumylperoxyl radical proceed via a one-step hydrogen atom and oxygen atom transfer rather than via an electron transfer from substrates to cumylperoxyl radical.

Photosensitized oxidation of furans; Part 18: A simple method for a one-pot synthesis of functionalized methyl cis-4-oxoalk-2-enoates

Functionalized methyl cis-4-oxoalk-2-enoates 2 are synthesized in a one-pot procedure by singlet oxygen oxygenation of the corresponding 2-methoxyfurans 1 in methanol and reduction of the resulting hydroperoxides 4 and 5 by the sulfides 6 which are selectively oxidized into the sulfoxides 7. The synthetic method has a wide range of applicability and affords compounds 2 stereoselectively and in good yields; concomitantly the sulfoxides 7 are obtained in excellent yields.

The Titanium Dioxide Sensitised Photo-Oxidation of Sulphides

Titanium dioxide has been shown to photosensitise the oxidation of sulphides to give sulphoxides and sulphones.Evidence is presented against the involvement of singlet oxygen and in favour of the sulphide radical cations as being intermediates.