193097-47-1

Upstream product

• 4837-01-8 1-bromo-2-phenylthioethane 
• 86428-23-1 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine 

Downstream Products

• 593-60-2 Vinyl bromide 
• 882-33-7 diphenyldisulfane 
• 193097-50-6 di-t-butyl 2-(2-propenyl)-2-[2-chloro-2-(phenylsulfonyl)ethyl]propanedioate 
• 193097-49-3 di-t-butyl 2-(2-propenyl)-2-[2-chloro-2-(phenylsulfinyl)ethyl]propanedioate 
• 193097-48-2 di-t-butyl 2-(2-propenyl)-2-[2-(phenylsulfinyl)ethyl]propanedioate 

Relevant academic research and scientific papers

Pyrolysis of α- and β-heteroatoms substituted ethyl phenyl sulfoxides

A study on the mechanism of the thermal decomposition of α- and β-heteroatoms substituted ethyl phenyl sulfoxides was carried out using 1-chloroethyl phenyl sulfoxide (1); two diastereomeric 1-acetoxyethyl (substituted phenyl) sulfoxides (2a) and (2b); and 2-chloroethyl phenyl, 2-bromoethyl phenyl, and 2-methoxyethyl phenyl sulfoxides (3, 4, 5). The rate of pyrolysis of 1 was 4.8 times faster at 160°C than that of ethyl phenyl sulfoxide used as a reference, while those of 2a and 2b were 107 and 155 times faster, respectively. The results indicate that the lone pair of electrons on the α-heteroatoms has a larger rate acceleration effect than the electronegativity of them. The substituent effects of the phenyl group of 2a and 2b gave positive Hammett ρ-values (ρa= 0.76 and ρb= 0.80 vs. σ). Activation parameters for 2a and 2b are as follows: 2a, ΔH?= 112 kJmol-1, ΔS?= -20 JK-1mol-1; 2b, ΔH?= 107 kJmol-1, ΔS?= -29 JK-1mol-1. Large deuterium kinetic isotope effects for 1-acetoxyethyl-2,2,2-d3 phenyl sulfoxides (2ad and 2bd) were observed (kH/kD= 3.5 ～ 4.1). These results suggest that the pyrolysis of -heteroatom substituted ethyl phenyl sulfoxides proceeds via a five-membered transition state deviated to E1-like in character. On the other hand, from the results of kinetics for the pyrolysis of 3, 4, and 5, no effect by the β-halogen atoms or some deceleration effect by the β-methoxy group was observed. Thus the reaction seems to proceed via an E1-like mechanism. Copyright Taylor & Francis Group.

Generation and intramolecular cyclization of α-sulfinyl and α-sulfonyl radicals

α-Phenylsulfinyl and α-Phenylsulfonyl radicals are generated by the reactions of α-chlorosulfoxides and α-chlorosulfones with tributyltin hydride, respectively. High reaction concentration (0.2 M) is required to ensure efficient generations of these radic