66613-07-8

Upstream product

• 69798-75-0 1-chloro-4-methyl-3-phenylthio-2-pentanone 
• 127-08-2 potassium acetate 
• 85660-52-2 3-chloro-4-methyl-3-phenylthio-2-pentanone 
• 64-19-7 acetic acid 
• 5682-80-4 3-bromo-4-methyl-pent-3-en-2-one 
• 108-98-5 thiophenol 
• 87505-76-8 Trifluoro-acetic acid 3-methyl-1-methylene-2-phenylsulfanyl-but-2-enyl ester 
• 22805-23-8 3-(phenylthio)pentane-2,4-dione 
• 75-16-1 methylmagnesium bromide 
• 6212-77-7 1-phenylthio-1-propyne 
• 87505-58-6 2-Methyl-3-phenylsulfanyl-penta-3,4-dien-2-ol 
• 87505-70-2 Trifluoro-acetic acid 1,1-dimethyl-2-phenylsulfanyl-buta-2,3-dienyl ester 

Relevant academic research and scientific papers

NUCLEOPHILIC SUBSTITUTION OF α-HALO-KETONES-XXII ACETOLYSIS OF α'-PHENOXY-α-CHLORO-KETONES. A COMPARISON OF THEIR REACTIVITY WITH THAT OF THE CORRESPONDING THIOETHERS

The results obtained in the acetolysis of α-chloro-ketones 1 a-e are compared with those previously reported for the acetolysis of the corresponding α'-phenylthio-α-chloro-ketones 15a-e and discussed in terms of the enolization-solvolysis mechanisms.

The Use of 1-Phenylthioprop-1-yne as an Equivalent of Phenylthiopropanone in Aldol Condensations

Addition of 1-lithio-1-phenylthiopropa-1,2-diene (7) to ketones, followed by trifluoroacetylation, a 3,3-rearrangement, and methanolysis of the resulting dienol trifluoroacetates, leads to the C-3 homologated α-phenylthioenones (2a) in 31-66percent overal

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.

THE AdNSNE MECHANISM IN THE REACTION OF PHENOL AND BENZENETHIOL WITH α-BROMO MICHAEL ACCEPTORS IN THE K2CO3-ACETONE SYSTEM

In the reaction of α-bromo Michael acceptors with either phenol or benzenethiol formal substitution of the vinylic bromine proceeds through addition of the phenolic reagent, followed by nucleophilic substitution and β-elimination (AdNSNE mechanism) in the system K2CO3-acetone.The process is shown to be stereospecific in the case of 2a,b and 3b,c, leading to the corresponding Z isomer.The reactivity of substrates 1-4 is discussed in terms of their structural features.