13079-28-2Relevant academic research and scientific papers
A facile procedure for preparation of carboxylic sulfonic anhydrides under solvent-free conditions
Hajipour,Mazloumi
, p. 137 - 141 (2003)
A manipulatively one-pot and rapid method for the synthesis of carboxylic sulfonic anhydride from acid chloride or sulfonyl chloride and potassium salt of carboxylic or sulfonic acid under solvent-free conditions is reported. The reaction has been carried out in excellent yield and short reaction time in the presence of DABCO under solvent-free conditions.
A simple synthesis of ketone from carboxylic acid using tosyl chloride as an activator
Jana, Samaresh,Sahoo, Debasis,Sarkar, Sohini
supporting information, (2019/09/06)
An effective process for the conversion of carboxylic acid to ketone has been discovered. In this process, carboxylic acid has been activated using p-toluene sulphonyl group. Under the optimized condition, aromatic, aliphatic heteroaromatic carboxylic acids have been proved to be good substrates for this methodology. The byproduct of this reaction can be removed very easily during work up process. Also, one equivalent of organometallic reagent is sufficient to complete this transformation.
A sequential one-pot tandem approach for the synthesis of 4-tosyl-5-aryloxazoles from carboxylic acids
Rajeev, Narasimhamurthy,Swaroop, Toreshettahally R,Anil, Seegehalli M,Kiran, Kuppalli R,Rangappa, Kanchugarakoppal S,Sadashiva, Maralinganadoddi P
, (2018/10/21)
Abstract: An efficient method for the synthesis of 4-tosyl-5-aryloxazoles directly from aromatic carboxylic acids has been reported. The method involves the conversion of aromatic carboxylic acids to tosyl carboxylates by treating with tosyl chloride in t
Kinetic investigation on the reactions of p-toluenesulfonyl chloride with p-substituted benzoic acid(s) in the presence of triethylamine in aprotic solvents
Ananthalakshmi, Subbiah,Nallu
experimental part, p. 303 - 308 (2009/10/17)
Second-order rate constants of the reactions of p-toluenesulfonyl chloride with p-substituted benzoic acids in the presence of triethylamine in acetonitrile/acetone under equimolar and pseudo-first-order conditions have been determined by the conductometric method using the Guggenheim principle at 25, 30, 35, and 40°C. The reactions follow second order with respect to the whole and first order with respect to each of the reactants. The order of reactivity of the substituents in benzoic acid is rationalized. Activation parameters are obtained by applying the usual methods. The Hammett plot has been found nonlinear, whereas the Bronsted plot shows good correlation. This may be explained on the basis of electronic effects of substituents on the reaction center. Kinetic data and the product analyses indicate that the reaction proceeds through direct nucleophilic attack on the sulfur center. Int J Chem Kinet 41: 303-308, 2009
Phase-Transfer Catalyzed Synthesis of Amides and Esters of Carboxylic Acids
Jaszay, Zsuzsa M.,Petnehazy, Imre,Toeke, Laszlo
, p. 745 - 747 (2007/10/02)
A convenient one-pot procedure is reported for the preparation of carboxamides and carboxylic acid esters from carboxylic acids and amines or alcohols, respectively.The carboxylic acids are activated by sulfonyl chlorides under solid-liquid phase-transfer conditions using solid potassium carbonate as base and a lipophilic quaternary ammonium salt as catalyst.
Sulphonic Acid-induced Fragmentation of Dialkyl Acylphosphonates, Formation of Alkyl Carboxylates and Alkyl Sulphonates
Breuer, Eli,Karaman, Rafik,Goldblum, Amiram,Leader, Haim
, p. 2029 - 2034 (2007/10/02)
Heating of dialkyl acylphosphonates with sulphonic acids under anhydrous conditions leads to the formation of alkyl sulphonates and alkyl carboxylates. 31P N.m.r. spectroscopy revealed that the reaction of equimolar amounts of dimethyl benzoylphosphonate (1) and toluene-p-sulphonic acid at room temperature gives dimethyl phosphonate (6) in 50percent yield.It is proposed that the by-product of this reaction, benzoic toluene-p-sulphonic anhydride (8), reacts with the excess of toluene-p-sulphonic acid, to yield toluene-p-sulphonic anhydride (9) and benzoic acid.Heating of these two compounds with dimethyl phosphonate was shown to yield methyl toluene-p-sulphonate and methyl benzoate, respectively.A postulated by-product of these reactions is phosphenous acid (HPO2).Quantum mechanical calculations by the MNDO/H method carried out on dimethyl benzoylphosphonate and its protonation products show that the preferred site of protonation of dimethyl benzoylphosphonate is the P=O oxygen, and that protonation at this site is followed by C-P bond breaking, with zero energy of activation, leading to dimethyl phosphite and benzoylium cation.
