7315-50-6

Upstream product

• 109-79-5 n-butanethiol 
• 100-52-7 benzaldehyde 
• 6425-08-7 4,4'-(phenylmethylene)bismorpholine 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 20025-27-8 β-phenylvinyl butyl sulfide 
• 772-01-0 2-phenyl-1,3-dioxane 
• 63935-93-3 benzoyltriethylsilane 
• 132868-67-8 (tert-butyldimethylsilyl)(phenyl)methanone 
• 123290-13-1 phenyltriisopropylsilylmethanone 

Downstream Products

• 629-45-8 dibutyl disulfide 
• 100-52-7 benzaldehyde 
• 77953-85-6 bis-(butane-1-sulfonyl)-phenyl-methane 

Relevant academic research and scientific papers

Direct anodic (thio)acetalization of aldehydes with alcohols (thiols) under neutral conditions, and computational insight into the electrochemical formation of the acetals

A versatile protocol for the production of acetals/thioacetals by means of direct electrochemical oxidation is developed here under neutral conditions, providing (thio)acetals with good functional group tolerance and a wide scope for both aldehydes and (thio)alcohols. DFT calculations reveal that direct electron transfer from the anode plays a key role in carbonyl activation during this acid free acetalization process.

Pot-economy autooxidative condensation of 2-Aryl-2-lithio-1,3-dithianes

The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.

Silicon benzoyl a method for preparing benzaldehyde thio-acetal

The invention provides a method for preparing benzaldehyde sulfo-acetal through benzaldehyde silicon, and relates to the field of preparation of sulfur compounds and silicon compounds. The benzaldehyde silicon and alkyl sulfhydryl (including primary merca

Silica-PCl5: A novel heterogenous catalyst for simple and efficient chemoselective protection of carbonyl compounds

A simple, efficient and environmentally benign procedure has been developed for chemoselective protection of carbonyl compounds using the newly developed heterogeneous catalyst: Silica-PCl5. A variety of aldehydes and ketones were efficiently c

Heteropoly acids as heterogeneous catalysts for thioacetalization and transthioacetalization reactions

Heteropoly acids are effective solid catalysts for the thioacetalization of carbonyl compounds. Tungstophosphoric acid (H3PW12O40), was found to be an effective and a highly selective catalyst for the thioacetalization of aldehydes, ketones and for the transthioacetalization of acetals, acylals and O,S-acetals which proceeded in excellent yields in the absence of solvent. The catalyst has also been successfully applied to the chemoselective conversion of α- or β-diketones and a β-keto ester into the corresponding dithioacetals. Sterically hindered carbonyl compounds such as camphor and benzophenone were also converted to their corresponding thioacetals in refluxing petroleum ether in 89-94percent yields. Surprisingly, anthrone was reduced to anthracene in 91percent yield.

2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS) and bromine as efficient catalysts for dithioacetalization and oxathioacetalization of carbonyl compounds and transdithioacetalization reactions

The use of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS), and bromine as efficient catalysts for conversion of carbonyl compounds to their cyclic and acyclic dithioacetals and 1,3-oxathiolanes under mild reaction conditions are described. These catalysts are also used for efficient transdithioacetalization of acetals, diacetals, ketals, acylals, enamines, hydrazones, and oximes with high yields in the presence of thiols.

Highly efficient transdithioacetalization of acetals catalyzed by silica chloride

A modified procedure for the preparation of a silica chloride with higher chloride capacity than that reported is described. Moreover, this silica chloride was found to be an effective catalyst for chemoselective and highly efficient transdithioacetalization of different classes of acetals.

A simple and convenient catalytic procedure for the preparation of dithioacetals

A simple procedure for the synthesis of cyclic and acyclic thioacetals from aldehydes is described which employs hydrogen chloride solutions generated from acetyl chloride and methanol. It was observed that the reaction could be carded out using catalytic quantities of acetyl chloride, potentially allowing acid sensitive substrates to be used under these conditions.

Chemoselective Protection of Aldehydes as Dithioacetals in Lithium Perchlorate-Diethyl Ether Medium. Evidence for the Formation of Oxocarbenium Ion Intermediate from Acetals

Aldehydes and acetals were very efficiently converted to acyclic and cyclic dithioacetals in 5 M lithium perchlorate/diethyl ether (LPDE) medium at ambient temperature in high yields.Spectroscopic and other experimental evidences strongly suggest the formation of oxocarbenium ion intermediates from acetals in 5 M LPDE which subsequently reacted with thiols to give the dithioacetals.Under the same conditions ketones and their acetals also reacted, albeit very slowly compared to aldehydes and acetals, to yield dithioacetals.The difference in their reactivity was successfully employed in the chemoselective dithioacetalization of aldehydes and acetals in the presence of ketones and their acetals.The chemoselective dithioacetalization of keto aldehydes has been realized with the keto group remaining intact.The present method offers a convenient, efficient, and neutral medium for the deprotection of acetals to aldehydes and also the chemoselective protection of aldehydes to dithioacetals.

EFFECTS OF SUBSTITUENTS AND MEDIUM ON ACIDITY OF α,α-BIS(BUTYLSULFONYL)TOLUENES

Seven substituted α,α-bis(butylsulfonyl)toluenes and three 2-aryl-1,1,3,3-tetraoxo-1,3-dithiolanes have been prepared and their 1H NMR, IR, and MS spectra measured.The pKHA values of the substituted α,α-bis(butylsulfonyl)toluenes have been determined by potentiometric titration in dimethyl sulfoxide, dimethylformamide, and 80percent (v/v) mixture of dimethyl sulfoxide and water.The results are intterpreted by the Yukawa-Tsuno relationship (parameter r = 0.43 - 0.49) and classified in relation to analogous N- and O-acids by the methods with latent variables (the method of conjigated deviations).