41159-07-3Relevant 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.
Selective arylthiolane deprotection by singlet oxygen: A promising tool for sensors and prodrugs
Lamb, Brian M.,Barbas, Carlos F.
supporting information, p. 3196 - 3199 (2015/05/27)
A routine thioketal protecting group reacts rapidly and selectively with singlet oxygen to reveal ketone products in good (aryl 1,3-dithiolane) to excellent (aryl 1,3-oxathiolane) yields. Arylthiolanes are stable to biologically relevant reactive oxygen species and can be used as a light-activated gating mechanism for activating fluorescent sensors or small molecule prodrugs.
Application of BU4N+HSO4- as an ionic liquid and acid catalyst for thioacetalization of aldehydes and ketones
Hajipour, Abdol R.,Hosseini, Peyman,Ruoho, Arnold E.
experimental part, p. 2502 - 2508 (2009/08/07)
A variety of carbonyl containing compounds have been successfully reacted with 1,2-ethanedithiol in a thioacetylization reaction using tetrabutylammonium hydrogensulfate as a mild and efficient catalyst. Aldehydes and ketones react with good to excellent