67395-06-6Relevant academic research and scientific papers
Highly ordered mesoporous functionalized pyridinium protic ionic liquid framework as a highly efficient catalytic system in chemoselective thioacetalization of carbonyl compounds under solvent-free conditions
Karimi, Nafiseh,Luque, Rafael,Rajabi, Fatemeh,Voskressensky, Leonid
, (2021/10/04)
Dithioacetals are a well-known class of organic compounds as both protecting group for the carbonyl compounds and valuable synthons for organic synthesis. Polysiloxane acidic ionic liquids containing pyridinium trifluoroacetate salts (PMO-Py-IL) as organi
Catalytic application of sulfamic acid-functionalized magnetic Fe3O4nanoparticles (SA-MNPs) for protection of aromatic carbonyl compounds and alcohols: Experimental and theoretical studies
Khaef, Sepideh,Taherpour, Avat Arman,Yarie, Meysam,Zolfigol, Mohammad Ali
, p. 44946 - 44957 (2020/12/30)
Protection techniques of functional groups within the structure of organic compounds are important synthetic methods against unwanted attacks from various reagents during synthetic sequences. Acetal and thioacetal groups are well known as protective funct
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.
Aluminum hydrogen sulfate [Al(HSO4)3] as an efficient catalyst for the preparation of thioacetals
Ghashang, Majid
, p. 2837 - 2842 (2013/07/26)
Aluminum hydrogen sulfate, as a heterogeneous solid acid catalyst, has been used for the mild conversion of carbonyl compounds to their thioacetals using 1,2- and 1,3-dithiol under ambient conditions with short reaction times in high to excellent yield in
Chemoselective dithioacetalization of carbonyl compounds using magnesium hydrogensulfate as efficient heterogeneous catalyst
Shaterian, Hamid Reza,Hosseinian, Asghar,Ghashang, Majid,Khorami, Fahimeh
experimental part, p. 2490 - 2501 (2009/08/07)
Carbonyl compounds have been successfully converted into their corresponding dithiolanes and dithianes derivatives with 1,2-ethanedithiol and 1,3-propanedithiol in excellent yield at room temperature and short reaction times using a catalytic amount of ma
An efficient, continuous flow technique for the chemoselective synthesis of thioacetals
Wiles, Charlotte,Watts, Paul,Haswell, Stephen J.
, p. 7362 - 7365 (2008/03/13)
By optimizing a reagent's residence time within a packed-bed reactor, it is possible to overcome selectivity issues frequently encountered in stirred reaction vessels. This important feature is demonstrated for the chemoselective protection of 4-acetylben
Chemoselective thioacetalization using 3-(1,3-dithian-2-ylidene)pentane-2, 4-dione as an odorless and efficient propane-1,3-dithiol equivalent under solvent-free conditions
Ouyang, Yan,Dong, Dewen,Zheng, Chunbai,Yu, Haifeng,Liu, Qun,Fu, Zhenqian
, p. 3801 - 3804 (2008/02/09)
As a non-thiolic, odorless propane-1,3-dithiol equivalent, 3-(1,3-dithian-2-ylidene)pentane-2,4-dione has been investigated in acid-promoted thioacetalization under solvent-free conditions. A range of selected aldehydes and aliphatic ketones have been converted into the corresponding dithioacetals in high yields. The relatively slow reaction rate of aromatic ketones allowed chemoselective protection of aromatic aldehydes or aliphatic ketones, in contrast to aromatic ketones. Georg Thieme Verlag Stuttgart.
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.
Chemoselective thioacetalization with odorless 2-(1,3-dithian-2-ylidene)-3- oxobutanoic acid as a 1,3-propanedithiol equivalent
Yu, Haifeng,Dong, Dewen,Ouyang, Yan,Liu, Qun
, p. 1741 - 1745 (2007/10/03)
Odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid (1c) was prepared and investigated in the thioacetalization of carbonyl compounds as a 1,3-propanedithiol equivalent. The results showed that the thioacetalization of various carbonyl compounds 2 with 1c proceeded smoothly and afforded the corresponding dithioacetals 3 in high yields (up to 99%) in the presence of acetyl chloride at room or reflux temperatures. Moreover, the thioacetalization exhibited high chemoselectivity between aldehydes and ketones.
Odorless thioacetalization reagent 2-[1,3] dithian-2-ylidene-3-oxo- butanamide and its chemoselectivity
Liu, Jun,Liu, Qun,Yu, Haifeng,Ouyang, Yan,Dong, Dewen
, p. 4545 - 4556 (2007/10/03)
2-[1,3]Dithian/dithiolan-2-ylidene-3-oxo-butanamide 2a/2b were synthesized and investigated in the thioacetalization reaction of aldehydes/ketones 3. The experiments revealed that 2a could be used as a nonthiolic, odorless 1,3-propanedithiol equivalent in the conversion of aldehydes/ketones into the corresponding dithianes 4, however, 2b was less effective. Moreover, the chemoselectivity of the thioacetalization of 3 in the presence of 2a is discussed.
