- 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
-
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
- Karimi, Nafiseh,Luque, Rafael,Rajabi, Fatemeh,Voskressensky, Leonid
-
-
- Catalytic application of sulfamic acid-functionalized magnetic Fe3O4nanoparticles (SA-MNPs) for protection of aromatic carbonyl compounds and alcohols: Experimental and theoretical studies
-
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
- Khaef, Sepideh,Taherpour, Avat Arman,Yarie, Meysam,Zolfigol, Mohammad Ali
-
p. 44946 - 44957
(2020/12/30)
-
- Selective arylthiolane deprotection by singlet oxygen: A promising tool for sensors and prodrugs
-
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.
- Lamb, Brian M.,Barbas, Carlos F.
-
supporting information
p. 3196 - 3199
(2015/05/27)
-
- Aluminum hydrogen sulfate [Al(HSO4)3] as an efficient catalyst for the preparation of thioacetals
-
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
- Ghashang, Majid
-
p. 2837 - 2842
(2013/07/26)
-
- Chemoselective dithioacetalization of carbonyl compounds using magnesium hydrogensulfate as efficient heterogeneous catalyst
-
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
- Shaterian, Hamid Reza,Hosseinian, Asghar,Ghashang, Majid,Khorami, Fahimeh
-
experimental part
p. 2490 - 2501
(2009/08/07)
-
- An efficient, continuous flow technique for the chemoselective synthesis of thioacetals
-
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
- Wiles, Charlotte,Watts, Paul,Haswell, Stephen J.
-
p. 7362 - 7365
(2008/03/13)
-
- 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
-
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.
- Ouyang, Yan,Dong, Dewen,Zheng, Chunbai,Yu, Haifeng,Liu, Qun,Fu, Zhenqian
-
p. 3801 - 3804
(2008/02/09)
-
- Chemoselective thioacetalization with odorless 2-(1,3-dithian-2-ylidene)-3- oxobutanoic acid as a 1,3-propanedithiol equivalent
-
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.
- Yu, Haifeng,Dong, Dewen,Ouyang, Yan,Liu, Qun
-
p. 1741 - 1745
(2007/10/03)
-
- Chemoselective thioacetalization in water: 3-(1,3-dithian-2-ylidene) pentane-2,4-dione as an odorless, efficient, and practical thioacetalization reagent
-
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.
- Dong, Dewen,Ouyang, Yan,Yu, Haifeng,Liu, Qun,Liu, Jun,Wang, Mang,Zhu, Jing
-
p. 4535 - 4537
(2007/10/03)
-
- Odorless thioacetalization reagent 2-[1,3] dithian-2-ylidene-3-oxo- butanamide and its chemoselectivity
-
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.
- Liu, Jun,Liu, Qun,Yu, Haifeng,Ouyang, Yan,Dong, Dewen
-
p. 4545 - 4556
(2007/10/03)
-
- α,α-diacetyl cyclic ketene dithioacetals: Odorless and efficient dithiol equivalents in thioacetalization reactions
-
Two novel, non-thiolic, odorless dithiol equivalents, α,α- diacetyl cyclic ketene dithioacetals 2a and 2b, had been developed. A range of carbonyl compounds 3 were converted into corresponding dithioacetals, dithianes 4 and dithiolanes 5, in high yields (up to 99%) in the presence of 2a or 2b. Moreover, 2a and 2b show high chemoselectivity between aldehyde and ketone in thioacetalization.
- Yu, Haifeng,Liu, Qun,Yin, Yanbing,Fang, Qunxin,Zhang, Jingping,Dong, Dewen
-
p. 999 - 1002
(2007/10/03)
-
- The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization
-
2-[2-Chloro-1-(1-chlorovinyl)allylidene]-1,3-dithiane 1 was synthesized by the chlorination of 3-(1,3)-dithianylidenepentane-2,4-dione 2 using the Vilsmeier-Haack reagent in 99% yield. As a novel nonthiolic, odorless 1,3-propane-dithiol equivalent, 1 was investigated in the thioacetalization reaction. Various types of aldehydes and ketones 3 were converted to the corresponding dithianes 4 in the presence of 1 in high yields (79-97%). Moreover, 1 exhibited obvious chemoselectivity between aldehyde and ketone in this thioacetalization reaction. A mechanism for this thioacetalization reaction is proposed.
- Liu, Qun,Che, Guangbo,Yu, Haifeng,Liu, Yingchun,Zhang, Jingping,Zhang, Qian,Dong, Dewen
-
p. 9148 - 9150
(2007/10/03)
-
- Mechanism of the Broensted Acid Catalysed Hydrolysis of 2-Aryl-2-methyl-1,3-dithianes in Aqueous Perchloric acid
-
The acid catalysed hydrolysis of five para-substituted 2-aryl-2-methyl-1,3-dithianes in aqueous perchloric acid (3-9 mol dm-3) has been studied kinetically.The effect of changes in substituents (ρ = -3.1), temperature (ΔS(excit.) = -38-60 J K-1 mol-1) and acidity (m(excit.) = 0.54-0.74), and the solvent isotope effects (kobsD2O/kobsH2O E2 mechanism for the MeO, Me, H and Cl derivatives.For the p-NO2 compound the acidity dependence, and the values of ΔH(excit.) and ΔS(excit.) (ca. -200 J K-1 mol-1) suggest a change to an A2-like mechanism.Our results are discussed in the light of previous work on acetal hydrolysis.
- Ali, Muhammad,Satchell, Derek P. N.
-
p. 219 - 222
(2007/10/02)
-
- COMPETITION BETWEEN ADDITION AND REDOX PROCESSES IN REACTIONS OF NITROARENES WITH LITHIUM-DITHIANES
-
The reaction of 2-lithio-1,3-dithianes with nitroarenes gives 2-(or 4-)cyclohexa-3,5(or 2,5-)-diene-1-nitronate compounds (conjugate-addition products), free nitroarene radical anions (redox products), 1,3-dithianes and 2,2'-bis-(1,3-dithianes).The conjugate-addition and redox products were converted in the respective nitroaromatic compounds by oxidation in situ with O2 or DDQ.The ratio between addition and redox products increases with decrease of temperature. 2-H-2-Lithio-1,3-dithiane can give both 1,4- and 1,6-addition products, while 2-methyl- and 2-phenyl derivatives give only 1,6-addition products.A mechanism involving an s.e.t. from lithium dithianes to nitroarenes followed by various decay routes is suggested for the two radical species.
- Bartoli, Giuseppe,Dalpozzo, Renato,Grossi, Loris,Todesco, Paolo E.
-
p. 2563 - 2570
(2007/10/02)
-