5849-03-6Relevant articles and documents
Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN
Yao, Yunxin,Zhao, Guangkuan,Hamze, Abdallah,Alami, Mouad,Provot, Olivier
, p. 5775 - 5779 (2020/08/17)
A mild process using a combination of TMSCl and NaI in acetonitrile is used to regenerate carbonyl compounds from a variety of dithiane and dithiolane derivatives. This easy to handle and inexpensive protocol is also efficient to deprotect oxygenated and mixed acetals as 1,3-dioxanes, 1,3-dioxolanes and 1,3-oxathianes quantitatively. As a possible extension of this method, it was also shown that nitrogenated substrates such as hydrazones, N-tosylhydrazones, and ketimines reacted well under these conditions to give the expected ketones in high yields. The methodology proposed herein is a good alternative to the existing methods since it does not use metals, oxidants, reducing agents, acidic or basic media, and keto-products were obtained in high to excellent yields.
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.
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
Iranpoor, Nasser,Firouzabadi, Habib,Shaterian, Hamid Reza,Zolfigol
, p. 1047 - 1071 (2007/10/03)
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.