20451-53-0Relevant articles and documents
Oxidation of aryl vinyl sulfides in the Butooh-Ti(OPri)4-(R,R)-diethyl tartrate system
Shainyan,Danilevich
, p. 1825 - 1827 (1998)
Oxidation of aryl vinyl sulfides into aryl vinyl sulfoxides in the ButOOH-Ti(OPri)4-(R, R)-diethyl tartrate system was studied. The process afforded low optical yields (no more than 5%). A model of the oxidation was proposed that allows interpreting the dependence of the reaction enantioselectivity on the structure of a substrate.
Accelerated Oxidation of Organic Sulfides by Microdroplet Chemistry
Li, Jia,Liu, Chengyuan,Chen, Hao,Zare, Richard N.
, p. 5011 - 5015 (2021/04/02)
We report the rapid oxidation of organic sulfides to sulfoxides by means of microdroplet chemistry at room temperature using a spray solution containing an organic sulfide dissolved in water/methanol, dilute (11%-14%) sodium hypochlorite (NaClO), and 5% chloroauric acid (HAuCl4). Ultrasonic nebulization, easy ambient sonic-spray ionization, or electrosonic spray ionization serves as the microdroplet source. High-resolution mass spectrometry was used as an online detector, and nuclear magnetic resonance was used as an offline detector. We found that the sulfoxide yields vary between 66 and 95%, the highest rate of product formation is 195 mg/min for benzyl phenyl sulfoxide, and the time required is a few minutes, which is much less than that required for the conventional means of achieving this chemical transformation. We also applied this microdroplet method to protein fingerprinting. We found that protein sequences containing methionine can be quickly oxidized, providing useful information for protein structure determinations.
Continuous bioinspired oxidation of sulfides
Crociani, Letizia,Mangiavacchi, Francesca,Marini, Francesca,Sancineto, Luca,Santi, Claudio
, (2020/07/02)
A simple, efficient, and selective oxidation under flow conditions of sulfides into their corresponding sulfoxides and sulfones is reported herein, using as a catalyst perselenic acid generated in situ by the oxidation of selenium (IV) oxide in a diluted aqueous solution of hydrogen peroxide as the final oxidant. The scope of the proposed methodology was investigated using aryl alkyl sulfides, aryl vinyl sulfides, and dialkyl sulfides as substrates, evidencing, in general, a good applicability. The scaled-up synthesis of (methylsulfonyl)benzene was also demonstrated, leading to its gram-scale preparation.
