72653-47-5

Upstream product

• 930-69-8 sodium thiophenolate 
• 1126-80-3 (n-butylthio)benzene 

Downstream Products

• 75697-53-9 (1-Methoxy-butylsulfanyl)-benzene 
• 72653-68-0 2-methyl-2-<1-(phenylthio)butyl>-1-cyclopentanone 
• 6891-45-8 2-Butyl-4-methylphenol 
• 6676-26-2 4-Butyl-2,6-dimethyl-phenol 
• 82209-87-8 4,4'-butylidenebis(2,6-xylenol) 
• 72653-58-8 2-(1-phenylthiobutyl)-δ-valerolactone 
• 229467-67-8 1-phenyl-2-(phenylthio)-1-pentene 
• 72653-67-9 2-(1-phenylthiobutyl)cyclopentanone 
• 105473-15-2 (1R,2S)-1-Phenyl-2-phenylsulfanyl-pentan-1-ol 
• 105473-15-2 (1S,2S)-1-Phenyl-2-phenylsulfanyl-pentan-1-ol 
• 17269-95-3 4-Butyl-2-methylphenol 
• 17269-96-4 butylhydroxytoluene 
• 6483-60-9 2-Butyl-4,6-dimethyl-phenol 
• 1638-22-8 4-n-butylphenol 

Relevant academic research and scientific papers

Thioalkylation of Enolates, III. Stereoselective Synthesis of Steroids and Related Compounds, II. α-Thioalkylation of Zinc Dienolates to 4-Substituted 1-tert-Butoxy-7a-methyl-hexahydroinden-5-ones

α-Alkylation of the α,β-unsaturated ketone 1 at C-4 has been achieved by thioalkylation of the corresponding zinc dienolate with α-chlorosulfides of type 2.The desulfurization of the β-(phenylthio)ketones 4 leads directly to the 4-substituted hexahydroind

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

Thioalkylation of Enolates, II. α-Thioalkylation of Zinc Enolates to α,α-Disubstituted Ketones

An α-alkylation of the 2-methylcycloalkanones 1 and 4 at the higher substituted carbon can be achieved by thioalkylation of the corresponding zinc enolates with the α-chlorosulfides 3.The desulfurization can be carried out with either Raney nickel or lithium in diethylamine for compounds which contain double or triple bonds. Key Words: Zinc enolates, thioalkylation of / Ketones, α,α-disubstituted / Desulfurization

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.

A New Syntethic Route to Vinyl Sulfides Utilizing the Reaction of (Phenylthio)carbenes with Nitrile Anions

Reactions of nitrile anion (LiCR2R3CN) and (phenylthio)carbenes generated from 1-chloroalkyl phenyl sulfides (R1CH(Cl)SPh) 2a-e by the action of n-BuLi have been shown to be a useful synthetic route to vinyl sulfides (PhSC(R1)=CR2R3) 3a-k (34-91percent).The nucleophilic attack of the nitrile anion on the carbenic species gave the presumed intermediate β-(phenylthio)-β-lithionitrile, which eliminated LiCN to give the expected vinyl sulfides.The application of the present reaction to the synthesis of cyclic vinyl sulfides was successful: the decomposition of the dianion ofω,ω-bis(phenylthio)alkanenitriles (8b, 8c, 11, and 14) affording the corresponding 1-(phenylthio)cycloalkenes (9, 10, 12, and 15) in 12-87percent yields.

Stereospecific Rearrangement of 2,2-Disubstituted Vinylsilane Epoxides to the Silyl Enol Ethers of 2,2-Disubstituted Aldehydes

The Z- and E-2-ethyl-2-methylvinylsilane epoxides (5a) and (5b) rearrange stereospecifically in the presence of boron trifluoride-diethyl ether to the Z- and E-silyl enol ethers, (6a) and (6b), respectively, of 2-methylbutanal.These silyl enol ethers reac

Some uses of silicon compounds in organic synthesis

1.The amount of γ-phenylthioalkylation of silyl dienol ethers is increased when the triphenylsilyl ether is used in place of the trimethylsilyl ether.Phenylthiomethylation is the least γ-selective carbon electrophile of several tried so far. 2.The acid-catalysed reactions of a range of γ-silyl tertiary alcohols cleanly give rearrangement, in which the silyl group controls the outcome.The reactions are similar in several respects to the rearrangements of the corresponding pinacols, except that the silicon controlled reactions are usually cleaner and give higher yields.The reaction is particularly useful for setting up quaternary carbon atoms.

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.