56819-81-9

Upstream product

• 13557-24-9 1-chloroethyl phenyl sulfide 
• 100-52-7 benzaldehyde 
• 4661-46-5 2-carboxybenzene diazonium chloride 
• 98204-56-9 (2R,3R)-3-Methyl-2-phenyl-1-oxa-4-thia-spiro[4.5]decane 
• 107978-06-3 (R)-1-phenyl-2-(phenylthio)propan-1-one 
• 622-38-8 Ethyl phenyl sulfide 
• 108-98-5 thiophenol 
• 4436-22-0 1-phenylpropylene oxide 

Downstream Products

• 4541-87-1 cis-1-phenylpropene oxide 
• 106026-92-0 threo-1-acetoxy-1-phenyl-2-phenylthiopropane 

Relevant academic research and scientific papers

The versatility of α-chloropropargyl phenyl sulfide affords high stereo- and regioselectivities in indium-promoted coupling reactions under mild conditions

Coupling reactions between α-chloropropargyl phenyl sulfide (11) and a series of aldehydes under aqueous conditions are reported. Not only is good stereoselectivity observed between syn and anti isomeric products, but excellent regioselectivity is also witnessed. In reactions using indium metal as a promoter, the propargyl functionality (12) is retained, unlike the use of more traditional metals that result in formation of products containing a mixture of both propargyl (12) and allene (13) moieties. The reaction is postulated to proceed via either a chelated or nonchelated route, controlled by the presence or absence of indium (111) chloride, and may be used to create synthetically useful building blocks. The formation of epoxyalkyne (14) molecules, which are found in many natural products and have wide use as synthetic templates, is presented as one example.

Use of α-chlorosulfides in indium promoted C-C couplings: Easy entry into the stereoselective formation of epoxy alkynes

The use of α-chlorosulfide compounds to control stereoselectivity in indium promoted C-C couplings occurs smoothly at room temperature under aqueous and mixed aqueous/organic conditions. Use of the halide to control synlanti ratios simplifies the indium p

Reaction of (α-Thioalkyl)chromium Compounds Prepared by Chromium(II) Reduction of α-Halo Sulfides

Reduction of α-chloroalkyl phenyl (or methyl) sulfides with chromium(II) chloride in THF proceeds smoothly in the presence of LiI.The resulting (α-thioalkyl)chromium reagents add to aldehydes in a chemo- and stereoselective manner.

Asymmetric Sulfenylation of Tin(II) Enolates of Ketones and 3-Acyl-2-oxazolidones. Application to the Synthesis of Optically Active Epoxides

In the presence of chiral diamines, the reaction between tin(II) enolates of ketones or 3-acyl-2-oxazolidones and thiosulfonates proceeds smoothly to give the corresponding β-keto sulfides with high enetioselectivity.Further, optically active epoxides are prepared from these β-keto sulfides.

Regiochemistry of Nucleophilic Opening of β-Substituted Styrene Oxides with Thiolate Anions: Model Experiments in the Synthesis of Leukotriene Analogues

β-Substituted trans-styrene oxides are cleaved with thiolate anions highly regioselectively by attack at the α-carbon whereas the cis-isomers are cleaved by attack at the α- and β-carbons.Cysteine, in a suitably protected form, similarly cleaves β-substituted trans-styrene oxides, thus allowing the synthesis of a simple LTE model.

BENZYNE-INDUCED FRAGMENTATION OF 1,3-OXATHIOLANES. A NOVEL METHOD FOR DEPROTECTION OF CARBONYL GROUPS, PREPARATION OF PHENYL VINYL SULFIDES, AND 1,2-CARBONYL TRANSPOSITION

A variety of 1,3-oxathiolanes undergo a benzyne-induced fragmentation leading to phenyl vinyl sulfides and carbonyl compounds.The reaction developed here provides a novel method for deprotection of carbonyl compounds from 1,3-oxathiolanes, preparation of phenyl vinyl sulfides, and 1,2-carbonyl transposition.