17334-45-1

Upstream product

• 14198-13-1 (3-(methylsulfinyl)propyl)benzene 
• 3277-89-2 phenethylmagnesium bromide 
• 74-88-4 methyl iodide 
• 637-59-2 1-Bromo-3-phenylpropane 
• 1821-12-1 4-Phenylbutyric acid 
• 1841512-58-0 1,3-dioxoisoindolin-2-yl 4-phenylbutanoate 
• 20277-69-4 sodium methansulfinate 
• 87231-07-0 methyl 3-phenylpropyl sulfide 

Downstream Products

• 300-57-2 allylbenzene 
• 17696-73-0 methylsulfinic acid 

Relevant academic research and scientific papers

Synthesis of Sulfones and Sulfonyl Derivatives using Sodium (tert-butyldimethylsilyl)oxymethanesulfinate

The present invention relates to a method for manufacturing a sulfone and sulfonyl derivative compound using sodium (tert-butyldimethylsilyl)oxymethanesulfinate, which is a novel organic sulfin salt, wherein the novel organic sulfin salt has good stability, environmental friendliness and economy, and is easy to handle, and thus significantly reduces the amount of transition metal catalysts and the amount of organic sulfin salts used when introducing aryl or alkenyl. Also, alkylation, arylation, amination, and fluorination are all possible during secondary functionalization. Therefore, the present invention can be usefully used in preparation and mass production of various kinds of sulfones and derivatives thereof including asymmetric sulfone derivatives.

Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives

An efficient protocol for the modular synthesis of sulfones and sulfonyl derivatives has been developed utilizing sodium tert-butyldimethylsilyloxymethanesulfinate (TBSOMS-Na) as a sulfoxylate (SO22-) equivalent. TBSOMS-Na, easily prepared from the commercial reagents Rongalite and TBSCl, serves as a potent nucleophile in S-alkylation and Cu-catalyzed S-arylation reactions with alkyl and aryl electrophiles. The sulfone products thus obtained can undergo the second bond formation at the sulfur center with various electrophiles without a separate unmasking step to afford sulfones and sulfonyl derivatives such as sulfonamides and sulfonyl fluorides.

Reaction of alkyl halides with rongalite: One-pot and telescoped syntheses of aliphatic sulfonamides, sulfonyl fluorides, and unsymmetrical sulfones

An efficient methodology has been developed for the one-pot or telescoped synthesis of aliphatic sulfonamides, sulfonyl fluorides, and unsymmetrical sulfones on the basis of interrupted alkylation of sodium hydroxymethylsulfinate (rongalite) with alkyl halides. The protocols are conducted under mild conditions, use inexpensive and shelf-stable reagents, and are not sensitive to air/moisture. These conditions can be applied in rapid parallel chemical synthesis, which was demonstrated by the preparation of a small sulfonamide library based on the core structure of the anticoagulant drug Tirofiban.

Ei elimination: An unprecedented facet of sulfone chemistry

Thermolysis of methyl 3-phenylpropyl sulfone in the gas phase results in formation of allylbenzene. Activation parameters of ΔH(+) = 53.5 ± 1.0 kcal/mol and ΔS(+) = -0.7 ± 1.4 cal/(mol·K) were obtained over the range of 490-550 °C. Similar measurements with a deuterated analogue show a substantial isotope effect, and a lower activation enthalpy is observed for the formation of styrene from methyl 2-phenylethyl sulfone. Along with high- quality ab initio calculations of activation parameters and kinetic isotope effects, these results indicate that this is the first reported Ei reaction of a simple sulfone.