34798-03-3

Upstream product

• 152141-79-2 (R)-(-)-s-butyl phenyl sulfide 
• 14905-79-4 1-methylpropyl phenyl sulfide 
• 100-58-3 phenylmagnesium bromide 
• 598-30-1 sec.-butyllithium 
• 73116-75-3 Trimethylsilyl Benzenesulfinate 
• 591-51-5 phenyllithium 
• 18522-92-4 sodium p-toluenesulfonamide 
• 1208-20-4 S-phenyl benzenethiosulfinate 
• 671795-46-3 sec-butylmagnesium bromide 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 76003-57-1 C₁₇H₂₁NO₃S₂ 
• 67833-44-7 2-Chlor-2-butyl-phenylsulfoxid 
• 14905-79-4 1-methylpropyl phenyl sulfide 

Relevant academic research and scientific papers

One-pot synthesis of α-phenylsulfinyl ketones by reaction of phenyl benzenethiosulfinate with enolate anions, and synthesis of sulfoxides and sulfides by its reaction with Grignard reagents

Phenyl benzenethiosulfinate reacts with enolate anions derived from ketones to give α-phenylsulfinyl ketones directly, together with minor amounts of α-phenylsulfanyl ketones. These are easily separated by forming the water-soluble sodium salts of the sulfinyl compounds. Grignard reagents also react with phenyl benzenethiosulfinate, to give mixtures of sulfoxides and sulfides.

One-Pot Sulfoxide Synthesis Exploiting a Sulfinyl-Dication Equivalent Generated from a DABSO/Trimethylsilyl Chloride Sequence

A one-pot process for the synthesis of unsymmetrical sulfoxides using organometallic nucleophiles is described. Sulfur dioxide, delivered from the surrogate DABSO (DABCO-bis(sulfur dioxide)), acts as the initial electrophile and combines with the first organometallic reagent to generate a sulfinate intermediate. In situ conversion of the sulfinate to a sulfinate silyl ester, using TMS-Cl (trimethylsilyl chloride), generates a second electrophile, allowing addition of a second organometallic reagent. Organolithium or Grignard reagents can be employed, delivering sulfoxides in good to excellent yields.

Selective oxidation of sulfides to sulfoxides using 30% hydrogen peroxide catalyzed with a recoverable silica-based tungstate interphase catalyst

(Chemical Equation Presented) Various types of aromatic and aliphatic sulfides are selectively oxidized to sulfoxides and sulfones in good to excellent yields using 30% H2O2 in the presence of catalytic amounts of a novel recoverable silica-based tungstate interphase catalyst at room temperature. The catalyst can be recovered and reused for at least eight reaction cycles under the described reaction conditions without considerable loss of reactivity.

1,1,1-Trifluoroacetone as an efficient catalyst for the hydrogen peroxide promoted selective oxidation of sulfides to sulfoxides

Organic sulfides are selectively oxidized to the corresponding sulfoxides in high yields and under very mild conditions using 35% hydrogen peroxide in CBCl3 in the presence of catalytic amounts of 1,1,1-trifluoroacetone.

Synthesis of sulfoxides by the oxidation of sulfides with sodium chlorite catalysed by manganese(III) acetylacetonate in acetone in the presence of alumina

Systematic oxidations of sulfides with sodium chlorite have been investigated in aprotic solvents under mild and neutral conditions.Metal catalysis is essential for the efficient oxidation, and conversion of a wide variety of diaryl, alkyl aryl, dialkyl and cyclic sulfides into the corresponding sulfoxides can be favoured by the catalytic presence of manganese(III) acetylacetonate in acetone with the aid of moist alumina in general or dry alumina in particular cases in a rapid, high-yielding manner.This simple procedure has also been found to be an easy method for chemoselective transformation of functionalised sulfides without extensive undesirable side-reactions.

STEREOCHEMISTRY OF SULPHILIMINE AND SULPHOXIDE FORMATIONS IN REACTIONS OF SULPHIDES WITH CHLORINATING AGENTS AND NUCLEOPHILES

The stereochemistry of sulphilimine and sulphoxide formations was studied in reactions of chiral alkyl aryl sulphides either with N-chloro toluenesulphonamides or with t-BuOCl followed by TsNH-Na+ both leading to unequal amounts of diastereomers of products.Configurations were determined by spectroscopic methods and stereospecific reactions, and diastereomeric product distributions were measured by hplc.Results are discussed and reaction pathways are suggested for-the product controlling steps.From sulphonium type intermediates sulphoxides are formed by hydrolysis with inversion, while sulphilimines with retention or inversion of configuration at sulphur depending on manner of attack by N-nucleophile.In reactions of ortho-carboxy-substituted sulphides both sulphilimines and sulphoxides are formed from cyclic acyloxysulphonium intermediates with inversion of configuration at sulphur.