ChemInform Abstract: Preparation of Esters and Amides from Carboxylic Acids by Activation with Dialkyl Phosphite-Carbon Tetrachloride Mixture.

ChemInform ◽  
2010 ◽  
Vol 29 (43) ◽  
pp. no-no
Author(s):  
Z. M. JASZAY ◽  
I. PETNEHAZY ◽  
L. TOKE
Keyword(s):  
Carbon Tetrachloride ◽  
Carboxylic Acids ◽  
Dialkyl Phosphite

CORRELATION OF O–H STRETCHING FREQUENCIES WITH pK VALUES FOR SOME PHENOLS

1957 ◽  
Vol 35 (12) ◽  
pp. 1555-1560 ◽  
Author(s):  
P. M. G. Bavin ◽  
William J. Canady
Keyword(s):  
Carbon Tetrachloride ◽  
Carboxylic Acids ◽  
Carbon Disulphide ◽  
Substituted Phenols ◽  
Electrostatic Effects ◽  
Single Straight Line ◽  
Linear Relationships ◽  
Straight Line ◽  
Alcohol Water

The O–H stretching frequencies, in carbon disulphide, of a number of phenols have been determined. Linear relationships were observed on plotting the stretching frequency against pKA in water. Polar substituted phenols were found to fall along one line, while phenols substituted with aliphatic groups were found to fall along another line of different slope. A change of slope is observed when the stretching frequencies of phenols are plotted against pKA measured in alcohol–water mixtures.Using Goulden's O–H stretching frequencies of carboxylic acids measured in carbon tetrachloride, an attempt has been made to explain the observed deviations from a single straight line in terms of electrostatic effects in the ionizing solvent. The results indicate that for the substances examined, such effects are not responsible for the observed deviations.

scholarly journals Atherton–Todd reaction: mechanism, scope and applications

2014 ◽  
Vol 10 ◽  
pp. 1166-1196 ◽  
Author(s):  
Stéphanie S Le Corre ◽  
Mathieu Berchel ◽  
Hélène Couthon-Gourvès ◽  
Jean-Pierre Haelters ◽  
Paul-Alain Jaffrès
Keyword(s):  
Reaction Mechanism ◽  
Carbon Tetrachloride ◽  
Primary Amine ◽  
Fire Retardant ◽  
Cross Coupling ◽  
Biological Applications ◽  
Dialkyl Phosphite ◽  
Reaction Conditions ◽  
Phenol Group ◽  
The Past

Initially, the Atherton–Todd (AT) reaction was applied for the synthesis of phosphoramidates by reacting dialkyl phosphite with a primary amine in the presence of carbon tetrachloride. These reaction conditions were subsequently modified with the aim to optimize them and the reaction was extended to different nucleophiles. The mechanism of this reaction led to controversial reports over the past years and is adequately discussed. We also present the scope of the AT reaction. Finally, we investigate the AT reaction by means of exemplary applications, which mainly concern three topics. First, we discuss the activation of a phenol group as a phosphate which allows for subsequent transformations such as cross coupling and reduction. Next, we examine the AT reaction applied to produce fire retardant compounds. In the last section, we investigate the use of the AT reaction for the production of compounds employed for biological applications. The selected examples to illustrate the applications of the Atherton–Todd reaction mainly cover the past 15 years.

Synthesis of Bridgehead Halides by Barton Halodecarboxylation

1989 ◽  
Vol 42 (1) ◽  
pp. 61 ◽  
Author(s):  
EW Della ◽  
J Tsanaktsidis
Keyword(s):  
Carbon Tetrachloride ◽  
Carboxylic Acids ◽  
Sodium Salt ◽  
Acid Chloride ◽  
Bromine Atom

Bridgehead carboxylic acids can be converted into their corresponding chlorides very efficiently under Barton halodecarboxylation conditions. Addition of the acid chloride to a suspension of the sodium salt of 1-hydroxypyridine-2(1H)- thione in boiling carbon tetrachloride under irradiation leads to excellent yields of the bridgehead chloride via the derived thiohydroxamic ester. In a useful modification for the synthesis of volatile halides, either 1,1,1-trichloro-2,2,2-trifluoroethane or trichlorofluoromethane can be employed as substitute solvents. It is found that the Barton procedure is applicable to the synthesis of labile bromides such as 1-bromobicyclo[3.1.1]heptane for which the usual Hunsdiecker reaction fails. For these, and other brominations , 2-bromo-2-chloro-1,1,1-trifluoroethane ('Halothane') is shown to function as an efficient solvent/bromine atom donor.

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