33487-46-6

Upstream product

• 14088-58-5 3-diazo-2-butanone 
• 931-59-9 benzenesulfenyl chloride 
• 1665-79-8 2,2,2-trimethoxy-4,5-dimethyl-2,2-dihydro-1,3,2-dioxaphosphole 
• 13023-53-5 3-phenylsulfanyl-butan-2-one 
• 17431-94-6 2-phenylsulfanyl-propionic acid 
• 108-98-5 thiophenol 

Downstream Products

• 19718-58-2 2-acetyl-2,5-bis(phenylthio)-6-methyl-3,4-dihydropyran 
• 13522-48-0 3-(phenylthio)-but-3-en-2-one 
• 29943-31-5 3-acetoxy-3-phenylthio-2-butanone 

Relevant academic research and scientific papers

Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives

The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.

NUCLEOPHILIC SUBSTITUTION OF α-HALO KETONES. XXI. STRUCTURE-REACTIVITY RELATIONSHIPS IN THE ACETOLYSIS OF 3-SUBSTITUTED 1-CHLORO-3-PHENYLTHIO-2-PROPANONES

The acetolyses of α-chloro ketones 1a-d have been re-investigated under standard conditions and compared with those of the corresponding isomeric substrates 2a-d.It has been shown that participation by the neighbouring phenylthio group, involving a 1-3 shift of the latter, does occur in part even in the case of 1d, while it is the only process in the case of 1e.A few structure-reactivity relationships in the two series of substrates are discussed.

NEW ACETYLENIC MICHAEL RECEPTOR EQUIVALENTS. PART I : SYNTHESIS OF α-SULFENYL - AND α-SULFINYL ACRYLIC DERIVATIVES.

The synthesis of α-thioarylated β-unsubstituted acrilic derivatives is reported.