137709-38-7Relevant academic research and scientific papers
Pot-economy autooxidative condensation of 2-Aryl-2-lithio-1,3-dithianes
Vale, Joao R.,Rimpil?inen, Tatu,Siev?nen, Elina,Rissanen, Kari,Afonso, Carlos A. M.,Candeias, Nuno R.
, p. 1948 - 1958 (2018/02/23)
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.
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.
Chemoselective dithioacetalization of carbonyl compounds using magnesium hydrogensulfate as efficient heterogeneous catalyst
Shaterian, Hamid Reza,Hosseinian, Asghar,Ghashang, Majid,Khorami, Fahimeh
experimental part, p. 2490 - 2501 (2009/08/07)
Carbonyl compounds have been successfully converted into their corresponding dithiolanes and dithianes derivatives with 1,2-ethanedithiol and 1,3-propanedithiol in excellent yield at room temperature and short reaction times using a catalytic amount of ma
Chemoselective dithioacetalization and oxathioacetalization of carbonyl compounds using alumina sulfuric acid as catalyst
Shaterian, Hamid Reza,Hosseinian, Asghar,Ghashang, Majid
experimental part, p. 4097 - 4106 (2009/04/11)
Carbonyl compounds have been successfully converted into their corresponding dithiolane, dithiane, and oxathiolane derivatives using a catalytic amount of alumina sulfuric acid (Al2O3-SO3H) with excellent yields at room temperature in short reaction times under mild conditions. This simple method is a highly chemoselective procedure for protection of aldehydes in the presence of ketones, and the heterogeneous catalyst can be recovered and reused several times without any loss of its activity. Copyright Taylor & Francis Group, LLC.
Trichloromelamine (TCM) - Catalyzed efficient and selective thioacetalization of aldehydes and transthioacetalization of acetals and oxathioacetals under mild reaction conditions
Hazarkhani, Hassan
, p. 2597 - 2606 (2008/12/22)
Trichloromelamine was used effectively as a catalyst for thioacetalization of aldehydes and transthioacetalization of acetals and oxathioacetals under mild and almost neutral reaction conditions. By this method, aldehydes, acetals, and oxathioacetals were selectively protected in the presence of ketones as their 1,3-dithiolanes or 1,3-dithianes. Copyright Taylor & Francis Group, LLC.
An efficient method for thioacetalization of carbonyl compounds in the presence of a catalytic amount of benzyltriphenylphosphonium tribromide under solvent-free conditions
Hajipour, Abdol R.,Pourmousavi, Seied A.,Ruoho, Arnold E.
, p. 921 - 937 (2008/02/05)
A variety of carbonyl compounds have been successfully converted to the corresponding thioacetal derivatives in good to excellent yields on the reaction of carbonyl compounds with 1,2-ethanedithiole, 1,3-propanedithiol, and ethanethiol in the presence of
Neutral lithium triflate (LiOTf) efficiently catalyzes chemoselective preparations of cyclic and acyclic dithioacetals from carbonyl compounds, acylals, and O,O-cyclic and open-chain acetals under solvent-free conditions
Firouzabadi, Habib,Eslami, Shahram,Karimi, Babak
, p. 2401 - 2406 (2007/10/03)
An efficient and chemoselective preparation of cyclic and acyclic thioacetals from carbonyl compounds, cyclic and acyclic acetals and acylals in the presence of catalytic amounts of neutral lithium triflate and thiols under solvent-free conditions is described.
A novel oxidative intramolecular [4+2]cycloaddition of silylene-protected dihydroxystyrene derivatives leading to peri-hydroxy polyclic aromatic compounds: A synthesis of the ABCD ring system of fredericamycin A
Kita,Okunaka,Honda,Kondo,Tamura,Tamura
, p. 2106 - 2114 (2007/10/02)
Heating of the silylene protected dihydroxystyrene generated from the o-hydroxyacetophenone (3a) at 130-150°C for 15-48 h in a sealed tube gave intramolecular [4+2]cycloaddition products (5 and 6). The addition of chloranil to the reaction mixture brought
