88087-86-9

Upstream product

• 61452-41-3 5-methyl-4-(phenylthio)-4,5-dihydrofuran-2(3H)-one 
• 71-36-3 butan-1-ol 
• 75717-32-7 cis-dihydro-5-methyl-4-(phenylthio)-2(3H)-furanone 
• 108378-43-4 butyl 3-butoxy-4-phenylthiopentanoate 

Downstream Products

• 88088-00-0 butyl 4-phenylthiopent-2-enoate 
• 88088-08-8 butyl 2,2-diethyl-4-phenylthiopent-3-enoate 
• 88088-09-9 butyl 4-phenylthio-2,2-dipropylpent-3-enoate 
• 88088-02-2 butyl 2-methyl-4-phenylthiopent-3-enoate 
• 88088-06-6 butyl 2,2-dimethyl-4-phenylthiopent-3-enoate 

Relevant academic research and scientific papers

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.

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.

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.