103603-55-0

Upstream product

• 1193-82-4 racemic methyl phenyl sulfoxide 
• 107-13-1 acrylonitrile 
• 407-25-0 trifluoroacetic anhydride 
• 54086-42-9 (phenylsulfinylmethyl)-tri-n-butyltin 
• 84140-28-3 1-(trimethylsilyl)-hept-2-yne 
• 100-47-0 benzonitrile 
• 75-05-8 acetonitrile 

Downstream Products

• 98-09-9 benzenesulfonyl chloride 

Relevant academic research and scientific papers

Sulfoxide-directed metal-free ortho-propargylation of aromatics and heteroaromatics

Abstract A sulfoxide-directed, metal-free ortho-propargylation of aromatics and heteroaromatics exploits intermolecular delivery of a propargyl nucleophile to sulfur followed by an intramolecular relay to carbon. The operationally simple cross-coupling procedure is general, regiospecific with regard to the propargyl nucleophile, and shows complete selectivity for products of ortho-propargylation over allenylation. The use of secondary propargyl silanes allows metal-free ortho-coupling to form carbon-carbon bonds between aromatic and heteroaromatic rings and secondary propargylic centres. The 'safety-catch' nature of the sulfoxide directing group is illustrated in a selective, iterative double cross-coupling process. The products of propargylation are versatile intermediates and they have been readily converted into substituted benzothiophenes. A sulfoxide-directed, metal-free ortho-propargylation of aromatics and heteroaromatics exploits intermolecular delivery of a propargyl nucleophile to sulfur followed by an intramolecular relay to carbon (see scheme). The process allows metal-free ortho-coupling to form carbon-carbon bonds between aromatic and heteroaromatic rings and propargylic centres.

Nucleophilic ortho-propargylation of aryl sulfoxides: An interrupted pummerer/allenyl thio-Claisen rearrangement sequence

A new direction: The nucleophilic ortho-propargylation of aryl sulfoxides exploits intermolecular delivery of the nucleophile to sulfur followed by an intramolecular relay to carbon (see scheme). The simple, metal-free procedure is general, regiospecific with regard to the propargyl nucleophile, and completely selective for products of ortho-propargylation over allenylation.

Sulfur(IV)-mediated transformations: From ylide transfer to metal-free arylation of carbonyl compounds

The development of a direct ylide transfer to carbonyl derivatives and of a sulfoxide-mediated arylation is presented from a unified perspective. Mechanistic studies (including density functional calculations) support a common reaction pathway and showcase how subtle changes in reactant properties can lead to disparate and seemingly unrelated reaction outcomes.

Sulfoxide-mediated α-arylation of carbonyl compounds

A novel sulfoxide-mediated α-arylation of carbonyl compounds is reported. This reaction proceeds under very mild conditions at room temperature and does not require any transition-metal promoter or catalyst.

Reduction of sulfoxides to sulfides mediated by ferrocene and trifluoroacetic anhydride

The reaction of diaryl sulfoxides with trifluoroacetic anhydride in the presence of ferrocene gives the corresponding sulfide. The reduction of sulfoxides composed of the ferrocene-spacer-methylsulfinyl triad system would proceed via a through-bond electron transfer rather than a through-space process.

Tin-Pummerer rearrangement in the synthesis of O,S-acetal derivatives

α-Thioalkyl esters and carbonates have been prepared by a tin-Pummerer rearrangement in reactions of α-stannylated sulfoxides with acid chlorides or chloroformates, respectively. Acid chlorides have a higher reactivity than chloroformates in this reaction. Acta Chemica Scandinavica 1997.

Remarkably Mild and Simple Preparations of Sulfinates, Sulfonyl Chlorides and Sulfonamides from Thioanisoles

New and high yielding procedures to convert thioanisoles into versatile sulfonyl chloride derivatives were developed by strategically taking advantage of the Pummerer reaction.

"Ene"-Type Reaction of the Pummerer Rearrangement Product Derived from 4-Chlorophenyl Methyl Sulphoxide: Synthesis of Some Insect Sex Pheromones

The Pummerer rearrengement product (8) derived from 4-chlorophenyl methyl sulphoxide (7) and trifluoroacetic anhydride undergoes an ene type reaction with terminal olefins to give the products (9).Oxidation of (9) followed by thermolysis of the resultant sulphoxides provides a general synthesis of the terminal conjugated dienes (10).Using this method, dodeca-9,11-dienyl acetate (16), the sex pheromone of the red bollworm moth, has been prepared.Transformations of the ene products (9) to some other insect sex pheromones such as bombykol (20) and tetradec-11-enyl acetate (24) are also described.

REACTION OF SULFOXIDES WITH NITRILES IN PRESENCE OF TRIFLUOROACETIC ANHYDRIDE AND TRIFLUOROACETIC ACID: A CASE OF RITTER REACTION OF PUMMERER INTERMEDIATE

Reaction of various sulfoxides 9, with nitriles 10 in presence of trifluoroacetic anhydride and trifluoroacetic acid gave the corresponding amides 11 via a Ritter reaction on Pummerer intermediate derived from the sulfoxides.