88087-83-6

Upstream product

• 623-70-1 ethyl (E)-crotonate 
• 931-59-9 benzenesulfenyl chloride 
• 52938-70-2 δ-phenylthio-γ-butyrolactone 
• 64-17-5 ethanol 
• 109542-07-6 ethyl 2-(phenylthio)but-3-enoate 
• 108-98-5 thiophenol 
• 77873-90-6 (Z) ethyl 2-phenylthiobut-2-enoate 
• 37746-78-4 4-bromo-trans-crotonic acid ethyl ester 

Downstream Products

• 88087-95-0 (E)-4-Phenylsulfanyl-but-3-enoic acid ethyl ester 
• 88087-97-2 ethyl 2-benzyl-2-methyl-4-phenylthiobut-3-enoate 
• 2960-66-9 4-oxo-but-2-enoic acid ethyl ester 
• 134418-79-4 ethyl 4-(phenylsulfonyl)-3-butenoate 
• 88087-95-0 ethyl 4-phenylthiobut-3-enoate 
• 121666-84-0 (E)-4-hydroxy-2-butenyl phenyl sulfide 
• 1403961-64-7 (E)-1-phenyl-4-(phenylthio)but-2-en-1-ol 
• 1403961-65-8 (E)-2-(4-(phenylthio)but-2-enyl)isoindoline-1,3-dione 
• 1403961-66-9 (E)-2-(3-(phenylthio)prop-1-enyl)-1,3-dioxolane 
• 1403961-78-3 N-(1-hydroxybut-3-en-2-yl)-4-methyl-N-(phenylthio)benzenesulfonamide 
• 1403961-81-8 N-(1-(1,3-dioxolan-2-yl)allyl)-4-methyl-N-(phenylthio)benzenesulfonamide 
• 124306-43-0 (E)-4-(phenylthio)but-2-enal 

Relevant academic research and scientific papers

Expanding the horizon of intermolecular trapping of in situ generated α-oxo gold carbenes: Efficient oxidative union of allylic sulfides and terminal alkynes via C-C bond formation

With a new P,S-bidentate phosphine as the ligand to gold(i), the α-oxo gold carbenes generated in situ via gold-catalyzed intermolecular oxidation of terminal alkynes were effectively trapped by various allylic sulfides, resulting in the formation of α-aryl(alkyl)thio-γ,δ- unsaturated ketones upon facile [2,3]sigmatropic rearrangements. This journal is the Partner Organisations 2014.

Catalyst-free imidation of allyl sulfides with chloramine-T and subsequent [2,3]-sigmatropic rearrangement

A facile synthesis of various allyl sulfonamides based on imidation of allyl sulfides with chloramine-T and subsequent [2,3]-sigmatropic rearrangement has been achieved without metal catalysts. The reaction completes smoothly within 10 min, providing excellent yields in environment friendly solvent of alcohol. Functional groups such as bromine, hydroxyl, protected amido and aldehyde are tolerant under this condition.

Reactions of α-or χ-Phenylthio Substituted Extended Enolate Anions Derived from Esters

The title anions are alkylated and acylated (α series only) exclusively at the α position.The α-phenylthio products give χ-phenylthio compounds by the PhS shift and the PhS group may be removed from the products in a number of ways.

Rearrangements of 2-Phenylthioethanols with Alkenyl, Alkynyl, Ester, and Other Functionalised Alkyl Substituents at the Migration Origin: Synthesis of γ-Phenylthiocrotonate Esters

The effects of functional groups near the migration origin in and PhS shifts are explored: an α-CO2R group prevents migration, α or β vinyl groups have only steric effects, alkynyl or CO2Et groups encourage rearrangement and provide routes to γ-phenylthio unsaturated esters and ketones.

EXTENDED ENOLATE IONS FROM γ-PHENYLTHIO-CROTONATE ESTERS

Substituted γ-phenylthio-crotonate esters (7) can be made by and PhS shifts: they form extended enolate anions which react with electrophiles at the carbon atom α to the carbonyl group and γ to sulphur.