42919-45-9

Usage

Chemical Properties

Yellow Liquid

InChI:InChI=1/C6H12OS2/c1-3-8-6(5-7)9-4-2/h5-6H,3-4H2,1-2H3

Upstream product

• 14044-67-8 (Z)-1,2-bis(ethylthio)ethene 
• 4396-19-4 bis(ethylthio)methane 
• 68-12-2 N,N-dimethyl-formamide 
• 79999-58-9 2,2-bis(ethylthio)-3,3-dimethyl-4-pentenal 
• 131543-46-9 Glyoxal 
• 75-08-1 ethanethiol 

Downstream Products

• 143136-45-2 (2R,4R)-2-(Bis-ethylsulfanyl-methyl)-4-phenyl-[1,3]dioxolane 
• 143136-45-2 (2S,4R)-2-(Bis-ethylsulfanyl-methyl)-4-phenyl-[1,3]dioxolane 
• 143136-43-0 (4R,5R)-2-(Bis-ethylsulfanyl-methyl)-4,5-dimethyl-[1,3]dioxolane 
• 76371-96-5 (2,2-Bis-ethylsulfanyl-vinyl)-cyclohexyl-amine 
• 76371-97-6 (2,2-Bis-ethylsulfanyl-vinyl)-phenyl-amine 
• 1234217-86-7 4,4-bis(ethylthio)-5-hydroxycyclohex-2-enone 
• 87921-13-9 2,2-bis(ethylthio)-5-phenylpent-4-enal 
• 96694-56-3 [2,2-Bis-ethylsulfanyl-5-methyl-hex-4-en-(E)-ylidene]-cyclohexyl-amine 
• 87921-15-1 2,2-bis(ethylthio)-2-(3-oxocyclohexyl)ethanal 
• 87647-27-6 2,2-bis(ethylthio)-3-phenylpropanenitrile 

Relevant academic research and scientific papers

Chemoselectivity as a delineator of cuprate structure in Catalytic 1,4-Addition of Diorganozinc reagents to michael acceptors

Reaction of the cyclic thioacetal (RS)2CHCHO [R = 1/2x-(CH 2)3] with HCCCOMe, followed by treatment with TsCl/DABCO (Ts = tosyl, DABCO= 1,4-diazabicyclo[2.2.2]octane) affords the mono-protected 1,4-benzoquinone dithioaceta

Enantioselective organocatalytic aldehyde-aldehyde cross-aldol couplings. The broad utility of α-thioacetal aldehydes

An asymmetric proline catalyzed aldol reaction with α-thioacetal aldehydes has been developed. Thioacetal bearing aldehydes readily participate as electrophilic cross-aldol partners with a broad range of aldehyde and ketone donors. High levels of reaction

A formal sigmatropic reaction involving free radical intermadiates: a mechanistic investigation

The quantitative isomerization of 2,2-bis(ethylthio)-3,3-dimethylpent-4-enal to 2,2-bis(ethylthio)-5-methylhex-4-enal was studied over the temperature range 130-170 deg C.An investigation of generality and specific mechanism of this formal sigmatropic shift was conducted with six related compounds.The rearrangements were found to obey first-order kinetics, and on the basis of significant positive entropies of activation (52-106 J deg-1 mol-1), crossover and trapping experiments, and the lack of a solvent effect (decane vs.DMF), an intermolecular, free-radical chain pathway has been proposed for the isomerization.During the rearrangement of several of the compounds esr signals were observed that were consistent with the presence of the proposed free-radical intermediates.These esr signals have been computer simulated.

Enamines of 2,2-bis(ethylthio)ethanal: a convenient route to γ-keto crotonate derivatives

A new α-oxoaldehyde reagent, 2,2-bis(ethylthio)ethanal 1, has been prepared in high yield from ethanedial.Alkylation of the potassium salt of the enamines of 1 with various alkylating agents followed by in situ hydrolysis of the intermediate imine afforded high yields of the alkylation products of 1.This new reagent was used in the synthesis of a chiral potential precursor of the macrocyclic fragment of cytochalasins A,B, and F, as well as in the syntheses of the physiologically active diolides pyrenophorin and norpyrenophorin.

Alkylation of Enamines of Bis(ethylthio)acetaldehyde: Synthesis of Norpyrenophorin

Alkylation of the potassium anion of the glyoxal derivatives (4) with halides and sulphonate esters, followed by acidic hydrolysis, provides good yields of the corresponding pyruvaldehyde α-thioacetals.