10359-08-7Relevant articles and documents
α,α-diacetyl cyclic ketene dithioacetals: Odorless and efficient dithiol equivalents in thioacetalization reactions
Yu, Haifeng,Liu, Qun,Yin, Yanbing,Fang, Qunxin,Zhang, Jingping,Dong, Dewen
, p. 999 - 1002 (2004)
Two novel, non-thiolic, odorless dithiol equivalents, α,α- diacetyl cyclic ketene dithioacetals 2a and 2b, had been developed. A range of carbonyl compounds 3 were converted into corresponding dithioacetals, dithianes 4 and dithiolanes 5, in high yields (up to 99%) in the presence of 2a or 2b. Moreover, 2a and 2b show high chemoselectivity between aldehyde and ketone in thioacetalization.
Highly efficient transdithioacetalization of acetals catalyzed by silica chloride
Firouzabadi, Habib,Iranpoor, Nasser,Karimi, Babak,Hazarkhani, Hassan
, p. 263 - 265 (2000)
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.
Polymer-assisted dithane hydrolysis with minimum workup
Luiken, Silke,Kirschning, Andreas
, p. 2018 - 2020 (2008)
(Chemical Equation Presented) The first solid-phase-assisted protocol for the hydrolysis of dithioacetals is described using three different functionalized ion exchange resins. The hydrolysis and the purification proceed under milder conditions than common homogeneously employed reagents so that very reactive carbonyl compounds can be prepared.
Ferric hydrogensulfate as effective and recyclable catalyst for mild dithioacetalization of aldehydes and ketones
Shaterian, Hamid Reza,Ahmadian, Hamid Reza,Ghashang, Majid,Doostmohammadi, Razieh,Yarahmadi, Hossein
, p. 1099 - 1108 (2008)
Ferric hydrogensulfate has been found to be an extremely efficient and recyclable heterogeneous catalyst for dithioacetalization reactions. Carbonyl compounds have been successfully converted into their corresponding dithiolanes and dithianes derivatives
The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization
Liu, Qun,Che, Guangbo,Yu, Haifeng,Liu, Yingchun,Zhang, Jingping,Zhang, Qian,Dong, Dewen
, p. 9148 - 9150 (2003)
2-[2-Chloro-1-(1-chlorovinyl)allylidene]-1,3-dithiane 1 was synthesized by the chlorination of 3-(1,3)-dithianylidenepentane-2,4-dione 2 using the Vilsmeier-Haack reagent in 99% yield. As a novel nonthiolic, odorless 1,3-propane-dithiol equivalent, 1 was investigated in the thioacetalization reaction. Various types of aldehydes and ketones 3 were converted to the corresponding dithianes 4 in the presence of 1 in high yields (79-97%). Moreover, 1 exhibited obvious chemoselectivity between aldehyde and ketone in this thioacetalization reaction. A mechanism for this thioacetalization reaction is proposed.
An expeditious synthesis of dithioacetals using zeolites
Kumar,Reddy,Singh,Pandey
, p. 67 - 69 (1993)
A simple and efficient catalytic method for dithioacetalization of various carbonyl compounds (saturated and α,β-unsaturated aliphatic, aromatic, heteroaromatic and hindered) with ethanethiol and 1,3-propanedithiol using H-Y and H-mordenite (H-M) zeolites
Preyssler-type heteropoly acid: A new, mild and efficient catalyst for protection of carbonyl compounds
Rahimizadeh, Mohammad,Bazazan, Tahmineh,Shiri, Ali,Bakavoli, Mehdi,Hassani, Hassan
, p. 435 - 438 (2011)
Preyssler-type heteropoly acid is introduced as a new, mild and efficient catalyst for protection of a variety of carbonyl compounds with 1,3-propane dithiol.
Chlorotrimethylsilane and Sodium Iodide: A Remarkable Metal-Free Association for the Desulfurization of Benzylic Dithioketals under Mild Conditions
Zhao, Guangkuan,Yuan, Ling-Zhi,Alami, Mouad,Provot, Olivier
, p. 2522 - 2536 (2018/05/14)
A novel metal-free process allowing the reductive desulfurization of various benzylic dithioketals to afford diarylmethane and benzylester derivatives with good to excellent yields is reported. At room temperature, this mild reduction process requires only the use of TMSCl and NaI in CH2Cl2 and tolerates a large variety of functional groups. (Figure presented.).
Palladium-catalyzed cross-coupling of 2-aryl-1,3-dithianes
Dockrey, Summer A. Baker,Makepeace, Alicia K.,Schmink, Jason R.
, p. 4730 - 4733 (2015/04/27)
Palladium-catalyzed cross-coupling of aryl bromides with 2-aryl-1,3-dithianes is described. This methodology takes advantage of the relatively acidic benzylic proton of the dithiane, allowing it to act as a competent, polarity-reversed transmetalation reagent. This unique approach affords the ability to employ an orthogonal deprotection strategy, and practical routes to both diaryl ketones and diarylmethanes are illustrated. Cross-coupling of a range of aryl dithianes with aryl bromides, including scope and current limitations, is presented.
