35031-56-2Relevant academic research and scientific papers
An efficient and green method for regio- and chemo-selective Friedel-Crafts acylations using a deep eutectic solvent ([CholineCl][ZnCl2]3)
Tran, Phuong Hoang,Nguyen, Hai Truong,Hansen, Poul Erik,Le, Thach Ngoc
, p. 37031 - 37038 (2016/05/24)
[CholineCl][ZnCl2]3, a deep eutectic solvent between choline chloride and ZnCl2, has been used as a dual function catalyst and green solvent for the Friedel-Crafts acylation of aromatic compounds instead of using the moisture-sensitive Lewis acids and volatile organic solvents. The reactions are performed with high yields under microwave irradiation with short reaction times for the synthesis of ketones. Interestingly, indole derivatives are regioselectively acylated in the 3-position under mild conditions with high yields without NH protection. Three new ketone products are synthesized. [CholineCl][ZnCl2]3 is easily synthesized from choline chloride and zinc chloride at a low cost, with easy purification and environmentally benign compounds. [CholineCl][ZnCl2]3 can be reused up to five times without loss of catalytic activity, making it ideal in industrial processes.
Gas-phase and solution basicities of some alkyl 2,6-dialkylphenyl ketones: A comparative analysis
Dell'erba, Carlo,Gruttadauria, Michelangelo,Mugnoli, Angelo,Noto, Renato,Novi, Marino,Occhiucci, Giorgio,Petrillo, Giovanni,Spinelli, Domenico
, p. 4565 - 4573 (2007/10/03)
The gas-phase basicity of a number of alkyl 2,6-dialkylphenyl ketones (2,6-R2C6H3COR') has been found to be almost insensitive to structural variations, as a result of a compensation of steric and electronic effects associated with the bulkiness and to the polarizability, respectively, of R and/or R'. On the contrary, the basicity in concentrated sulfuric acid undergoes, along the same series of compounds, a variation of nearly 8 pK units, as a consequence of steric inhibition of solvation of the protonated carbonyl as the main effect played by R and/or R'. The results in the condensed phase agree very nicely with recent findings relevant to some 4- substituted 2,6-dimethylacetophenones and 4-substituted acetophenones as well as with data for a large number of dialkyl or alkyl aryl ketones (either from the literature or determined herein) leading to an overall pK(BH+) vs. m* correlation (slope = 8.8, n = 31, r = 0.996; Eq. (3)) which appears to be of general significance and identifies steric inhibition of solvation as a common prevailing factor influencing the carbonyl basicity, at least in the absence of strong conjugative interactions. (C) 2000 Elsevier Science Ltd.
