135655-77-5Relevant academic research and scientific papers
Nickel(II) chloride as an efficient and useful catalyst for chemoselective thioacetalization of aldehydes
Khan, Abu T.,Mondal, Ejabul,Sahu, Priti R.,Islam, Samimul
, p. 919 - 922 (2003)
A wide variety of acyclic and cyclic dithioacetals can be prepared chemoselectively from the corresponding aldehydes by employing a catalytic amount of nickel(II) chloride in dry CH2Cl2-MeOH (5:1) at room temperature in good yields.
The directing group wins over acidity: kinetically controlled regioselective lithiation for functionalization of 2-(2,4-dihalophenyl)-1,3-dithiane derivatives
Sakthivel, Shanmugam,Kothapalli, Raveendra Babu,Balamurugan, Rengarajan
, p. 1670 - 1679 (2016/02/09)
Regioselective lithiation followed by functionalization of 2-(2,4-dihalophenyl)-1,3-dithiane derivatives with different electrophiles was achieved in good to excellent yields. When the title compound is treated with n-butyl lithium, lithiation occurs selectively at the aromatic carbon having less acidic proton despite the presence of thermodynamically more acidic 1,3-dithiane proton in the same molecule. Computationally calculated pKa values of the available reactive site protons and the experimental results suggest that the regioselective lithiation in 2-(2,4-dihalophenyl)-1,3-dithiane derivatives is not governed by thermodynamic acidity rather exclusively dictated by the kinetic removal of protons due to cooperative coordination (complex induced proximity effect, CIPE) and inductive effects of the 1,3-dihalo substituents present in the aromatic ring. By employing this regioselective functionalization, diverse 1,2,3,4-tetra-substituted aromatic compounds were prepared with ease.
Sulfonated polyanthracene-catalyzed highly efficient and chemoselective thioacetalization of carbonyl compounds and transthioacetalization of acetals and acylals
Fahid,Pourmousavi
, p. 16 - 29 (2015/10/20)
A straightforward and highly efficient procedure for the thioacetalization of a variety of aldehydes and transthioacetalization of acylals and acetals in good to excellent yields using catalytic amounts of sulfonated polyanthracene (S-PAT) is reported. Th
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
Efficient method for thioacetalization of carbonyl compounds in the presence of a catalytic amount of benzyltriphenylphosphonium tribromide (BTPTB) under solvent-free conditions
Hajipour, Abdol Reza,Pourmousavi, Seied A.,Ruoho, Arnold E.
, p. 2548 - 2566 (2008/12/22)
A variety of carbonyl compounds have been successfully converted to the corresponding thioacetal derivatives in good to excellent yields on reaction of carbonyl compounds with 1,2-ethanedithiole, 1,3-propanedithiol, and ethylthiol in the presence of a cat
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.
A simple and practical synthetic protocol for acetalisation, thioacetalisation and transthioacetalisation of carbonyl compounds under solvent-free conditions
Khan, Abu T.,Mondal, Ejabul,Ghosh, Subrata,Islam, Samimul
, p. 2002 - 2009 (2007/10/03)
A wide variety of carbonyl compounds can be converted smoothly to the corresponding acetals on treatment with alcohols or diols and triethyl orthoformate in the presence of a catalytic amount of (bromodimethyl)sulfonium bromide at room temperature. Similarly, various carbonyl compounds can be transformed into the corresponding dithioacetals on reaction with thiol or dithiols at room temperature by employing the same catalyst without any solvent. Moreover, O,O-acetals can also be converted into the corresponding dithioacetals under identical conditions. Some of the major advantages are mild reaction conditions, a high degree of efficiency, compatibilty with other protecting groups and the lack of solvents, particularly for thioacetalisation. In addition, no brominations occur at the double bond or α to the keto position or even in the aromatic ring under these experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Selective thioacetalization of aldehydes catalyzed by aqueous zinc tetrafluoroborate
Islam, Samimul,Majee, Adinath,Mandal, Tanmay,Khan
, p. 2911 - 2916 (2007/10/03)
A wide range of cyclic dithioacetals are prepared from the corresponding aldehydes in the presence of aqueous solution of zinc tetrafluoroborate.
2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS) and bromine as efficient catalysts for dithioacetalization and oxathioacetalization of carbonyl compounds and transdithioacetalization reactions
Iranpoor, Nasser,Firouzabadi, Habib,Shaterian, Hamid Reza,Zolfigol
, p. 1047 - 1071 (2007/10/03)
The use of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS), and bromine as efficient catalysts for conversion of carbonyl compounds to their cyclic and acyclic dithioacetals and 1,3-oxathiolanes under mild reaction conditions are described. These catalysts are also used for efficient transdithioacetalization of acetals, diacetals, ketals, acylals, enamines, hydrazones, and oximes with high yields in the presence of thiols.
