39854-49-4Relevant 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.
Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system
Inamoto, Kiyofumi,Yamada, Tetsuya,Kato, Sei-Ichi,Kikkawa, Shoko,Kondo, Yoshinori
, p. 9192 - 9199 (2013/10/01)
The combination of 1,4-benzoquinone and a catalytic amount of NaI was found to be effective for the deprotection of dithioacetals. The reactions proceeded efficiently under mild, near-neutral reaction conditions, producing a wide range of aryl and alkyl aldehydes and ketones generally in high yields with good functional group compatibility. The method developed therefore represents a general, facile, and highly applicable approach for deprotecting dithioacetals.
Chemoselective (trans)thioacetalization of carbonyl compounds with a reusable lewis acid-surfactant-combined copper bis(dodecyl sulfate) catalyst in water
Weng, Shiue-Shien,Chang, Shen-Chun,Chang, Tsuan-Hao,Chyn, Jong-Pyng,Lee, Shu-Wei,Lin, Chao-An,Chen, Fong-Kuang
experimental part, p. 1493 - 1499 (2010/10/03)
A Lewis acid-surfactant-combined copper bis(dodecyl sulfate) [Cu(DS) 2] catalyst served as an efficient and reusable catalyst for the thioacetalization and transthioacetalization of carbonyl compounds and O,O-acetals in water at room temperature. Some of the major advantages of this procedure are high chemoselectivity, ease of operation and purification without any organic solvent, and high yields. Georg Thieme Verlag Stuttgart.