Nucleophilic substitution with inversion of alcohol configuration with the reagent complex triphenylphosphine-diethyl azodicarboxylate-carboxylic acid. A convenient preparation of epicholesterol

1977 ◽  
Vol 42 (23) ◽  
pp. 3778-3779 ◽  
Author(s):  
Lorenzo P. L. Piacenza
Keyword(s):  
Carboxylic Acid ◽  
Nucleophilic Substitution ◽  
Diethyl Azodicarboxylate ◽  
Convenient Preparation

scholarly journals Development of variously functionalized nitrile oxides

2015 ◽  
Vol 11 ◽  
pp. 1241-1245 ◽  
Author(s):  
Haruyasu Asahara ◽  
Keita Arikiyo ◽  
Nagatoshi Nishiwaki
Keyword(s):  
Carboxylic Acid ◽  
Nucleophilic Substitution ◽  
Functional Groups ◽  
Grignard Reagent ◽  
Cycloaddition Reaction ◽  
Chemical Transformations ◽  
Nitrile Oxides ◽  
Weinreb Amide ◽  
Isoxazole Derivatives ◽  
Acid Esters

N-Methylated amides (N,4-dimethylbenzamide and N-methylcyclohexanecarboxamide) were systematically subjected to chemical transformations, namely, N-tosylation followed by nucleophilic substitution. The amide function was converted to the corresponding carboxylic acid, esters, amides, aldehyde, and ketone upon treatment with hydroxide, alkoxide, amine, diisobutylaluminium hydride and Grignard reagent, respectively. In these transformations, N-methyl-N-tosylcarboxamides behave like a Weinreb amide. Similarly, N-methyl-5-phenylisoxazole-3-carboxamide was converted into 3-functionalized isoxazole derivatives. Since the amide was prepared by the cycloaddition reaction of ethynylbenzene and N-methylcarbamoylnitrile oxide, the nitrile oxide served as the equivalent of the nitrile oxides bearing a variety of functional groups such as carboxy, alkoxycarbonyl, carbamoyl, acyl and formyl moieties.

ChemInform Abstract: Convenient Preparation of Acyltrimethylsilanes from Carboxylic Acid Derivatives.

ChemInform ◽  
1987 ◽  
Vol 18 (51) ◽  
Author(s):  
J. KANG ◽  
J. H. LEE ◽  
K. S. KIM ◽  
J. U. JEONG ◽  
C. PYUN
Keyword(s):  
Carboxylic Acid ◽  
Convenient Preparation
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