39854-49-4Relevant academic research and scientific papers
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.
SBA-15 functionalized sulfonic acid containing a confined hydrophobic and acidic ionic liquid: A highly efficient catalyst for solvent-free thioacetalization of carbonyl compounds at room temperature
Karimi, Babak,Vafaeezadeh, Majid
, p. 23207 - 23211 (2013/11/19)
A novel application of SBA-15 functionalized sulfonic acid containing a confined ionic liquid has been introduced to convert various carbonyl compounds to their corresponding dithioacetals and dithioketals at room temperature and under solvent-free condit
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.
Silica-supported phosphorus pentoxide: A reusable catalyst for S,S-acetalization of carbonyl groups under ambient conditions
Shaterian, Hamid Reza,Azizi, Kobra,Fahimi, Nafiseh
experimental part, p. 85 - 91 (2012/01/06)
Phosphorus pentoxide supported on silica gel (P2O 5/SiO2) efficiently acts as a highly active and reusable catalyst for cyclic and non-cyclic S,S-acetalization of a variety of carbonyl compounds under mild, solvent-free an
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.
Catalytic carbon-sulfur bond formation by amphoteric vanadyl triflate: exploring with thia-Michael addition, thioacetalization, and transthioacetalization reactions
Chen, Chien-Tien,Lin, Yow-Dzer,Liu, Cheng-Yuan
supporting information; experimental part, p. 10470 - 10476 (2010/02/28)
A series of thiols have been examined as protic nucleophiles for Michael-type additions to α,β-unsaturated carbonyls as well as double nucleophilic condensations with aldehydes, ketones, and acetals catalyzed by amphoteric, water-tolerant vanadyl triflate under mild and neutral conditions. The newly developed C-S bond formation protocols were carried out smoothly in good to high yields in a highly chemoselective manner.
Oxalic acid-promoted preparation of dithioacetals from carbonyl compounds or acetals
Miyake, Hideyoshi,Nakao, Yuichi,Sasaki, Mitsuru
, p. 104 - 105 (2007/10/03)
This letter describes oxalic acid-promoted syntheses of dithioacetals from carbonyl compounds and thiols. Acetals are also converted into dithioacetals by the reaction with thiols under similar conditions. Copyright
Bismuth oxide perchlorate as a highly efficient and chemoselective catalyst for thioacetalization of carbonyl compounds under solvent-free conditions
Sunil Kumar,Thirupathi Reddy,Narsimha Reddy,Rao,Rajitha
, p. 2387 - 2389 (2007/10/03)
Bismuth oxide perchlorate efficiently and chemoselectively catalyzes the thioacetalization of both aliphatic and aromatic carbonyl compounds under solvent-free conditions. Stearically hindered ketones are also thioacetalized in excellent yields with stoic
Highly efficient and chemoselective thioacetalization of carbonyl compounds catalyzed with aluminum trifluromethanesulfonate [Al(OTf)3]
Firouzabadi,Iranpoor,Kohmareh
, p. 167 - 173 (2007/10/03)
Aluminum trifluromethanesulfonate [Al(OTf)3] is a highly efficient and chemoselective catalyst for the thioacetalization of carbonyl compounds.
Trichloroisocyanuric acid as a mild and efficient catalyst for thioacetalization and transthio-acetalization reactions
Firouzabadi,Iranpoor,Hazarkhani
, p. 1641 - 1643 (2007/10/03)
Trichloroisocyanuric acid (1), a cheap industrial chemical, catalyzes mild and efficient thioacetalization and transthioacetalization reactions. In addition, this catalyst is very selective for this purpose.
