72653-49-7

Upstream product

• 7210-80-2 neopentyl phenyl sulphide 

Downstream Products

• 119704-14-2 (E)-2-(2,2-dimethylpropylidene)cyclohexanone 
• 72653-53-3 2-(2,2-dimethylpropyl)cyclohexanone 
• 109023-26-9 6,6-dimethyl-1-dimethyl(phenyl)silyl-5-phenylthioheptan-3-one 
• 109023-15-6 1-(Dimethyl-phenyl-silanyl)-2,6,6-trimethyl-heptan-3-one 
• 109023-16-7 1-(Dimethyl-phenyl-silanyl)-4,6,6-trimethyl-heptan-3-one 
• 109023-14-5 6,6-dimethyl-1-dimethyl(phenyl)silylheptan-3-one 
• 63996-46-3 Phenyl-(2-chlor-1,2-dimethyl)propyl-sulfid 
• 72653-52-2 2-(1-phenylthio-2,2-dimethylpropyl)cyclohexanone 
• 109023-25-8 6,6-dimethyl-5-phenylthiohept-1-en-3-one 

Relevant academic research and scientific papers

α-ALKYLATION AND α-ALKYLIDENATION OF CARBONYL COMPOUNDS BY O-SILYLATED ENOLATE PHENYLTHIOALKYLATION

For many reactions next to a carbonyl group, the use of O-silylated enolate chemistry offers improvements in yield and selectivity over the corresponding reactions of Group I metal enolates.In the case of α-alkylation of carbonyl compounds, Lewis acid (TiCl4 or ZnBr2) promoted phenylthioalkylation of O-silylated enolates 3 by α-chlorosulphides 4 (R3=H, Me, Prn, Pri, Bui, and Me3Si), followed by reductive sulphur removal by Raney nickel, 5->6, is found to be a reliable method for this synthetically important C-C bond forming step.An alternative sulphur elimination pathway via the sulphoxide, 5->7, allows the regio- and stereocontrolled α-alkylidenation of carbonyl compounds.The phenylthioalkylation reaction is applicable to ketones, aldehydes, esters, and lactones.

Ring Expansion or Spirocyclisation of (Phenylthiomethylene)cycloalkanes with Aluminium Chloride via β-Thio Carbocations

The title reactions can be explained by Wagner-Meerwein rearrangement of α-thio carbocations (thionium ions) to β-thio carbocations; this unusual reactivity may be due to superelectrophilic activation by aluminium chloride.

Thioalkylation of Enolates, IV. α-Alkylidenecyclopentanones by α-Alkylidation of Methyl 2-Oxocyclopentanecarboxylate

An α-alkylidation of cyclopentanone was achieved in two reaction steps in an overall yield of 20 to 79percent via a zinc chloride-catalyzed thioalkylation of the zinc enolate of methyl 2-oxocyclopentanecarboxylate (3) and subsequent saponification/desulfurization of the β-(phenylthio) ketone intermediates 5.For the saponification/desulfurization step DABCO proved to be the reagent of choice and superior to the use of alkali or magnesium halides. - Key Words: Zinc enolates, thioalkylation of / Cyclopentanones, α-alkylidene

α-Alkylation and α-alkylidenation of carbonyl compounds: Lewis acid-promoted phenylthioalkylation of o-silylated enolates

The O-silylated enolates of ketones, aldehydes, esters, and lactones can be phenylthioalkylated in the presence of Lewis acids; reductive or oxidative sulphur-removal gives the regiospecifically α-alkylated or alkylidenated carbonyl compounds.