206128-52-1

Upstream product

• 36304-27-5 tert-butyl 1-(p-tolylthio)acetate 
• 106-45-6 para-thiocresol 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 540-88-5 acetic acid tert-butyl ester 
• 672-78-6 methyl p-toluene sulfinate 
• 40723-30-6 (+)-(S)-allyl-p-toluenesulphinamide 

Downstream Products

• 256473-73-1 tert-butyl (2E)-4,4-diethoxy-2-[(4-methylphenyl)sulfinyl]but-2-enoate 

Relevant academic research and scientific papers

Intramolecular Pauson-Khand reactions of α,β-unsaturated esters and related electron-deficient olefins

The intramolecular Pauson-Khand (PK) reaction of a variety of electron-poor enynes having an ester, cyano, or phosphonate group at the olefin terminus is described. Depending on the reaction conditions and substitution at the enyne, their dicobalthexacarbonyl complexes led preferentially to the exocyclic 1,3-diene or to the PK cyclopentenone product. In general, the 1,3-diene was obtained as the major product under N-oxide-promoted conditions, while the PK product was selectively formed in refluxing acetonitrile.

Bis(1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane) peroxodisulfate: A mild and efficient oxidant for oxidation of thiols, sulfides and aromatic amines to the corresponding disulfides, sulfoxides and azo compounds

Bis(1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane) peroxodisulfate (BAABCPS) 1, readily prepared as orange solid from commercially available 1,4-diazabicyclo[2.2.2]octane (DABCO) and potassium peroxodisulfate converts thiols, sulfoxides and aromatic amines to the corresponding disulfides, sulfoxides and azo compounds respectively.

1,3-Cycloaddition of nitrile oxides to cyclic and open-chain 4-oxo-2- sulfinylbut-2-enoic acid derivatives

The reactions of tert-butyl (E)-4,4-diethoxy-2-p-tolylsulfinylbut-2- enoate with benzonitrile, acetonitrile, and bromoformonitrile oxides yield isoxazoles. However, (S5,S(s))- and (R5,S(s))-5-ethoxy-3-p- tolylsulfinylfuranones with benzonitrile oxide afford isoxazolines. The reactivity of the double bond as a dipolarophile is strongly increased by the sulfinyl group. This is also the case of the regioselectivity, which usually is opposite to that exhibited by dipolarophiles lacking the sulfinyl group. Electrostatic interactions seemingly explain this behaviour. The π-facial selectivity of the reactions with the cyclic dipolarophiles is dependent on steric effects, but some role seems to be exerted by electrostatic attraction.

1-Benzyl-1-aza-4-azoniabicyclooctane periodate as new oxidant for oxidation of thiols and sulfides to the corresponding disulfides and sulfoxides under anhydrous conditions

1-Benzyl-1-aza-4-azoniabicyclooctane periodate (BAABCOP) 1, readily prepared as an orange solid from commercially available DABCO (1,4-diazobicyclooctane) performs oxidation in anhydrous conditions. Under these conditions, thiols are selectively oxidised to disulfides. Sulfides are also oxidised to the corresponding sulfoxides under these conditions.

Solid state oxidation of aromatic sulfides to corresponding phenyl and p-tolyl sulfoxides and sulone using oxone

Phenyl and p-tolyl sulfides 1 can be selectively oxidised to the corresponding sulfoxides 2 or sulfones 3 in solid state condition using oxone. The advantages of this method are the use of cheap and safe reagents, high yield and simple operating conditions.

NUCLEOPHILIC SUBSTITUTION AT SULPHUR WITH RETENTION OF CONFIGURATION IN ALKYL-p-TOLUENESULPHINAMIDES

p-Tolylsulphinylacetates are formed with prevailing retention of configuration at sulphur and with enantiomeric excess (e.e.) up to 29percent in the reaction of sulphinamides 1a, 1b with α-bromo esters 2a, 2b in the presence of BuLi.