69178-10-5Relevant academic research and scientific papers
Direct anodic (thio)acetalization of aldehydes with alcohols (thiols) under neutral conditions, and computational insight into the electrochemical formation of the acetals
Liu, Caiyan,Shen, Yongli,Xiao, Zihui,Yang, Hui,Han, Xue,Yuan, Kedong,Ding, Yi
, p. 4030 - 4034 (2019/08/07)
A versatile protocol for the production of acetals/thioacetals by means of direct electrochemical oxidation is developed here under neutral conditions, providing (thio)acetals with good functional group tolerance and a wide scope for both aldehydes and (thio)alcohols. DFT calculations reveal that direct electron transfer from the anode plays a key role in carbonyl activation during this acid free acetalization process.
Solid-supported odorless reagents for the dithioacetalization of aldehydes and ketones
Jung,Gr?ssle,Lütjohann,Br?se
supporting information, p. 1036 - 1039 (2016/10/17)
A solid supported, odorless reagent for the dithioacetalization of aldehydes and ketones has been developed. The new reagent provides the dimercaptoalkane equivalent in combination with stoichiometric amounts of immobilized acid and enables the formation of dithianes and dithiolanes from aldehydes without any additives in good to very good yields with high purities. The reaction is chemoselective for aldehydes, but ketones can be reacted to the corresponding dithioketals if an additional Lewis acid such as BF3is added.
Stereoselective approaches to the total synthesis of (6R,4′S, 6′R)-cryptofolione
Sabitha, Gowravaram,Reddy, S. Siva Sankara,Reddy, D. Vasudeva,Bhaskar, Vangala,Yadav, Jhillu S.
body text, p. 3453 - 3460 (2010/11/20)
Total syntheses of cryptofolione were accomplished by two different routes via a common intermediate that underwent a cross-metathesis (CM) reaction with a vinyl lactone. The intermediate was prepared by coupling of an acyl anion equivalent with a chiral allyl epoxide synthon, or by Prins cyclization of a trans-cinnamaldehyde with a chiral homoallylic alcohol. Goniothalamin was obtained as a cross-metathesis product of the diacetate and vinyl lactone. 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.
Cleavage of 1,3-dithianes via acid-catalyzed hydrolysis of the corresponding 1,3-dithianemonooxides
Krohn, Karsten,Cludius-Brandt, Stephan
body text, p. 2369 - 2372 (2009/04/07)
The hydrolysis of 1,3-dithianes to their parent carbonyl compounds via their corresponding monosulfoxides was systematically investigated. The oxidation of the 1,3-dithianes was carried out in high yields using tert-butyl hydroperoxide. Acid-catalyzed hydrolysis of the monosulfoxides to the carbonyl compounds was then performed in excellent yields. The cleavage reactions were monitored by gas chromatography and kinetics were investigated on substrates varying in electron density and steric requirements. Neither effect prevented high overall yields in the cleavage reaction. Georg Thieme Verlag Stuttgart.
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.
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
1,3-Dithiane-derived alkoxyamines as one-carbon radical precursors
Herrera, Antonio J.,Studer, Armido
, p. 1389 - 1396 (2007/10/03)
A new method for the generation of C-2 centered radicals derived from 1,3-dithiane is presented. The radical precursors, 2-dialkylaminoxyl-1,3- dithianes, are readily prepared from 1,3-dithiane and stable nitroxides. Thermal reaction of 2-dialkylaminoxyl-1,3-dithianes with electron-deficient olefins affords carboaminoxylation products oroxidative addition products depending on the nitroxide used. The 2-dialkylaminoxyl-1,3-dithianes can also be used as initiators/regulators for the controlled living free radical polymerization of styrene. Georg Thieme Verlag Stuttgart.
A simple and practical synthetic protocol for thioacetalization of carbonyl compounds
Khan, Abu T.,Mondal, Ejabul
, p. 844 - 850 (2007/10/03)
Various aldehydes and ketones are smoothly converted to the corresponding acyclic and cyclic dithioacetals in very good yields by employing catalytic amount of acetyl chloride at room temperature under solvent-free conditions. Some of the major advantages of this procedure are its mild reaction conditions, highly efficient and selective, good yields, economically cheaper and compatible in the presence of a wide variety of other protecting groups.
Chemoselective thioacetalization in water: 3-(1,3-dithian-2-ylidene) pentane-2,4-dione as an odorless, efficient, and practical thioacetalization reagent
Dong, Dewen,Ouyang, Yan,Yu, Haifeng,Liu, Qun,Liu, Jun,Wang, Mang,Zhu, Jing
, p. 4535 - 4537 (2007/10/03)
A chemoselective thioacetalization utilizing 3-(1,3-dithian-2-ylidene) pentane-2,4-dione as a novel nonthiolic, odorless 1,3-propanedithiol equivalent catalyzed by p-dodecylbenze-nesulfonic acid in water has been developed.
