35531-58-9Relevant academic research and scientific papers
A simple and convenient catalytic procedure for the preparation of dithioacetals
Graham, Andrew E.
, p. 697 - 703 (1999)
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.
Visible-light mediated facile dithiane deprotection under metal free conditions
Dharpure, Pankaj D.,Bhowmick, Anindita,Warghude, Prakash K.,Bhat, Ramakrishna G.
, (2019/12/09)
Visible light mediated facile and selective dithiane deprotection under metal free conditions is developed. Eosin Y (1 mol%) proved to be an effective catalyst for the dithiane deprotection under the ambient photoredox conditions. The standard household compact fluorescent light source (CFL bulb) proved to be effective under open-air conditions in aqueous acetonitrile at room temperature. The protocol that exhibits a broad substrate scope and functional group tolerance has been shown to expand to a range of transformations for the electron-rich and -deficient thioacetals and thioketals. The synthetic utility of this protocol has also been demonstrated by gram-scale application.
Direct anodic (thio)acetalization of aldehydes with alcohols (thiols) under neutral conditions, and computational insight into the electrochemical formation of the acetals
Liu, Caiyan,Shen, Yongli,Xiao, Zihui,Yang, Hui,Han, Xue,Yuan, Kedong,Ding, Yi
, p. 4030 - 4034 (2019/08/07)
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.
A 2 - substituted - 1, 3 - dithiane derivative of the preparation method
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Paragraph 0023; 0024; 0025; 0026; 0027, (2019/06/26)
The invention provides a preparation method of a 2-substituted-1,3-dithiane derivative. The preparation method comprises the following steps: adding 1,3-dithiane (CAS:505-23-7) and 1,2-dichloroethane (DCE) or dichloromethane (DCM) into a reaction bottle, adding N-chlorosuccinimide (NCS) under ice-bath condition, and stirring for 0.5-1 h to prepare a 2-chloro-1,3-dithiane solution; and adding an aldehyde or ketone compound and a lewis acid catalyst into the above solution, and reacting to prepare the 2-substituted-1,3-dithiane derivative. By using the 1,3-dithiane solid and different types of aldehyde and keto-carbonyl compounds as raw material and using one or more of ferric trichloride, boron trifluoride diethyl etherate, methanesulfonic acid, aluminum trichloride, ferrous chloride and nickel chloride as catalysts, preparation of the 2-substituted-1,3-dithiane derivative is realized. The catalysts used in the invention are cheap and easily available, dosage of the catalysts is low and pollution of the catalysts is little. The solid raw materials used in the invention can avoid use of fetid toxic 1,3-dimercaptopropane with strong volatility, and the purpose of protecting an experimenter's body and reducing environmental pollution is realized. In addition, the preparation method has advantages of mild reaction condition, high yield, simple operation and the like.
Thioacetalization of aldehydes and ketones catalyzed by hexabromoacetone
Chaiseeda, Kittichai,Chavasiri, Warinthorn
, p. 1034 - 1039 (2017/09/08)
Protection of p-anisaldehydewith 1,3-propanedithiol under UV irradiation without a catalyst resulted in 87% yield of 1,3-dithiane in 20 min. Addition of hexabromoacetone further reduced the reaction time and UV irradiation also accelerated the formation o
Fe-catalyzed direct dithioacetalization of aldehydes with 2-chloro-1,3-dithiane
Lai, Junshan,Du, Wenbin,Tian, Lixia,Zhao, Changgui,She, Xuegong,Tang, Shouchu
, p. 4396 - 4399 (2015/01/08)
Present methods to synthesize 1,3-dithiane molecules require either harsh reaction conditions or highly specialized reagents. We have developed a catalytic dithioacetalization process that directly gains access to the corresponding 1,3-dithianes using aldehydes and 2-chloro-1,3-dithiane in a highly efficient manner. This methodology is beneficial due to mildness of the reaction conditions, and the dithioacetaliation process results in good to excellent yields by using 15 mol % of an iron catalyst.
Aluminum hydrogen sulfate [Al(HSO4)3] as an efficient catalyst for the preparation of thioacetals
Ghashang, Majid
, p. 2837 - 2842 (2013/07/26)
Aluminum hydrogen sulfate, as a heterogeneous solid acid catalyst, has been used for the mild conversion of carbonyl compounds to their thioacetals using 1,2- and 1,3-dithiol under ambient conditions with short reaction times in high to excellent yield in
Synthesis of 1,3-dithiane and 1,3-dithiolane derivatives by tungstate sulfuric acid: Recyclable and green catalyst
Karami, Bahador,Taei, Mahbubeh,Khodabakhshi, Saeed,Jamshidi, Masih
experimental part, p. 65 - 74 (2012/07/14)
An efficient, novel, and environmentally benign procedure for the thioacetalization of aliphatic and aromatic carbonyl compounds in the presence of catalytic amounts of tungstate sulfuric acid under solvent-free conditions to afford 1,3-dithianes and 1,3-
Palladium-catalyzed intramolecular aryl amination reaction: An expeditious approach to the synthesis of chiral benzodiazocine derivatives
Adhikary, Nirmal Das,Chattopadhyay, Partha
experimental part, p. 1754 - 1762 (2010/06/15)
A palladium-catalyzed method for intramolecular amination of aryl bromides and iodides has been developed employing different bulky biaryl phosphanes as ligands and toluene as solvent. A variety of electron-rich aryl halide substrates have been aminated b
A mild and chemoselective dithioacetalization of aldehydes in the presence of anhydrous copper (II) sulfate
Moghaddam, Firouz Matloubi,Bardajee, Ghasem Rezanejade,Oskui, Afsane Arefi
, p. 1445 - 1450 (2007/10/03)
Various aldehydes have been protected with different thiols as dithioacetals with excellent yields using anhydrous copper sulfate as a mild and chemoselective catalyst. The reaction is carried out in a solvent and/or under solvent-free conditions. The transthioacetalization of oxyacetals into dithioacetals was also achieved in an excellent yield. Copyright Taylor & Francis Group, LLC.
