ChemInform Abstract: Ceric Ammonium Nitrate (CAN) - A Useful Catalyst for the Rapid and High-Yield Esterification of Carboxylic Acids and Alcohols with Special Reference to Steroid and Other Multi-Functional Natural Products.

ChemInform ◽  
2001 ◽  
Vol 32 (16) ◽  
pp. no-no
Author(s):  
Papori Goswami ◽  
Pritish Chowdhury
Keyword(s):  
Natural Products ◽  
Special Reference ◽  
Ammonium Nitrate ◽  
Carboxylic Acids ◽  
Ceric Ammonium Nitrate ◽  
High Yield

Ceric Ammonium Nitrate Oxidation of Cyclic Ketones

1972 ◽  
Vol 50 (13) ◽  
pp. 2047-2052 ◽  
Author(s):  
P. Soucy ◽  
Tse-Lok Ho ◽  
P. Deslongchamps
Keyword(s):  
Ammonium Nitrate ◽  
Carboxylic Acids ◽  
Ceric Ammonium Nitrate ◽  
Cyclic Ketones

Ceric ammonium nitrate oxidation of cyclohexanone, cyclopentanone, and norbornanone gives nitrato-carboxylic acids, oxidation of adamantanone and adamantan-2-ol gives the lactone 14.

Ceric ammonium nitrate and manganese(III) acetate mediated radical oxidation and addition reactions of anthracene and 9-substituted anthracenes

2012 ◽  
Vol 31 (1) ◽  
pp. 55 ◽  
Author(s):  
Mustafa Zengin ◽  
Faith Sonmez ◽  
Mustafa Arslan ◽  
Mustafa Kucukislamoglu
Keyword(s):  
Ammonium Nitrate ◽  
Acidic Medium ◽  
Ceric Ammonium Nitrate ◽  
High Yield ◽  
Addition Reactions ◽  
Dimethyl Malonate ◽  
Radical Oxidation ◽  
Anthraquinone Derivatives ◽  
Anthracene Derivatives

Radical oxidation and addition reactions of anthracene (1), 9-methylanthracene (2) and 9-phenylanthracene (3) were investigated with dimethyl malonate (4) in the presence of ceric ammonium nitrate (CAN) and manganese(III) acetate (Mn(OAc)3). Although mostly anthraquinone derivatives and bianthrone were obtained with CAN, substituted 9,10-dihydroanthracene and 9,10-substituted anthracene derivatives were obtained with Mn(OAc)3. Dimethylmalonyl addition products (5a, 33 % and 5b, 42 %) were obtained in higher yield than quinones (5d, 8 % and 5e, 3 %) using Mn(OAc)3 as oxidant. 9a (96 %) and 9b (84 %) were synthesized in high yield and substitution products (7a, 44 % and 8b, 56 %) were obtained in higher yields than quinones (5d and 5e) using CAN as oxidant. The reactions were carried out in non-acidic medium (dichloromethane and methanol). Based on the structures of the isolated products a mechanism for these transformations was proposed.

scholarly journals Polyethylene Glycols as Efficient Media for Decarboxylative Nitration of α,β-Unsaturated Aromatic Carboxylic Acids by Ceric Ammonium Nitrate in Acetonitrile Medium: A Kinetic and Mechanistic Study

2013 ◽  
Vol 2013 ◽  
pp. 1-12 ◽  
Author(s):  
K. Ramesh ◽  
S. Shylaja ◽  
K. C. Rajanna ◽  
P. Giridhar Reddy ◽  
P. K. Saiprakash
Keyword(s):  
Ammonium Nitrate ◽  
Carboxylic Acids ◽  
Reaction Times ◽  
Ceric Ammonium Nitrate ◽  
Polyethylene Glycols ◽  
Mechanistic Study ◽  
Aromatic Carboxylic Acids ◽  
Detailed Kinetics ◽  
Kinetics Of ◽  
Acetonitrile Medium

Polyethylene glycols (PEGs) were found to be efficient media for decarboxylative nitration of α,β-unsaturated aromatic carboxylic acids by ceric ammonium nitrate (CAN) in acetonitrile to give β-nitrostyrene derivatives. Kinetics of the reaction exhibited second order kinetics with a first order dependence on [CAN] and [substrate]. Reactions were too sluggish to be studied in the absence of PEG; therefore detailed kinetics were not taken up. Reaction times were reduced from 24 hrs to few hours. The catalytic activity was found to be in the increasing order PEG-300 > PEG-400 > PEG-600 > PEG-200. Mechanism of PEG-mediated reactions was explained by Menger-Portnoy's scheme as applied in micellar kinetics.

scholarly journals Mechanically induced solvent-free esterification method at room temperature

RSC Advances ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 5080-5085
Author(s):  
Lei Zheng ◽  
Chen Sun ◽  
Wenhao Xu ◽  
Alexandr V. Dushkin ◽  
Nikolay Polyakov ◽  
...  
Keyword(s):  
Natural Products ◽  
Carboxylic Acids ◽  
Late Stage ◽  
Reaction Mechanisms ◽  
Room Temperature ◽  
Solvent Free ◽  
Mild Conditions

We have developed I2/KH2PO2 and KI/P(OEt)3 strategy syntheses of esters from carboxylic acids and alcohols through different reaction mechanisms. The advantages of present protocol: mild conditions and late-stage diversification of natural products.

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