Synthesis and stereochemistry of 5-substituted quinuclidine-2-carboxylic acids with semicyclic double bonds

1971 ◽  
Vol 4 (5) ◽  
pp. 636-639
Author(s):  
L. N. Yakhontov ◽  
L. I. Mastafanova ◽  
K. F. Turchin ◽  
T. D. Pervacheva ◽  
M. V. Rubtsov
Keyword(s):  
Carboxylic Acids ◽  
Double Bonds

One-Pot Synthesis of 2-Substituted Benzoxazoles Directly from Carboxylic Acids

2008 ◽  
Vol 61 (11) ◽  
pp. 881 ◽  
Author(s):  
Dinesh Kumar ◽  
Santosh Rudrawar ◽  
Asit K. Chakraborti
Keyword(s):  
Carboxylic Acids ◽  
Methanesulfonic Acid ◽  
Acid Chlorides ◽  
Double Bonds ◽  
Reaction Conditions ◽  
One Pot ◽  
Effective Catalyst ◽  
One Pot Synthesis ◽  
Highly Effective

Methanesulfonic acid has been found to be a highly effective catalyst for a convenient and one-pot synthesis of 2-substituted benzoxazoles by the reaction of 2-aminophenol with acid chlorides, generated in situ from carboxylic acids. Aryl, heteroaryl, and arylalkyl carboxylic acids provided excellent yields of the corresponding benzoxazoles. The reaction conditions were compatible with various substituents such as chloro, bromo, nitro, methoxy, cyclopentyloxy, phenoxy, thiophenoxy, and conjugated double bonds. Benzoxazole formation was found to be general with respect to substituted 2-aminophenols.

Permanganate Oxidation of Polybutadiene Rubbers

1951 ◽  
Vol 24 (3) ◽  
pp. 640-648
Author(s):  
F. J. Naples ◽  
J. D. D'Ianni
Keyword(s):  
Carbon Dioxide ◽  
Succinic Acid ◽  
Carboxylic Acids ◽  
Regular Structure ◽  
Emulsion System ◽  
Double Bonds ◽  
Permanganate Oxidation ◽  
Emulsion Polymer ◽  
Methods Of Analysis

Abstract In view of the failure to obtain quantitative yields of the expected carboxylic acids by permanganate oxidation of the several butadiene polymers studied, definite conclusions about their structures cannot be made. The results have a qualitative significance, however, in that the −10° emulsion polymer was found to produce a larger amount of succinic acid than the 50° emulsion polymer and less tricarballylic acid, and thus they correlate with general thinking that lowered temperature of polymerization results in a polymer of more regular structure and less branching. The Alfin polymer, although prepared in a system entirely different from the emulsion system, gave results which indicated a microstructure similar to that of 50° emulsion polybutadiene. Sodium polybutadiene was less completely characterized than the others, but the large amounts of carbon dioxide and β-carboxyadipic acid isolated correlated well with the high percentage of external double bonds known to be present from other methods of analysis.

scholarly journals Cp*CoIII-Catalyzed C–H Functionalization and Asymmetric Reactions Using External Chiral Sources

Synlett ◽  
2019 ◽  
Vol 30 (12) ◽  
pp. 1384-1400 ◽  
Author(s):  
Tatsuhiko Yoshino ◽  
Shigeki Matsunaga
Keyword(s):  
Carboxylic Acids ◽  
Asymmetric Reactions ◽  
Addition Reactions ◽  
Double Bonds ◽  
Cyclization Reactions ◽  
Catalytic Asymmetric ◽  
Allyl Alcohols

This account describes Cp*CoIII-catalyzed C–H functionalization reactions developed in our group between 2013 and 2018. Cp*CoIII catalysts not only serve as inexpensive alternatives to Cp*RhIII catalysts but also exhibit unique reactivity and selectivity in several transformations. In the latter part of this review, we introduce catalytic asymmetric C–H functionalization reactions using achiral RhIII or CoIII catalysts with chiral disulfonates or carboxylic acids as external chiral sources.1 Introduction and Overview2 Cp*CoIII-Catalyzed C–H Functionalization Reactions2.1 C–H Addition Reactions to Polar Double Bonds2.2 Cp*Co(CO)I2 and [Cp*CoI2]2 Precursors for the C2-selective C–H Amidation of Indoles2.3 C–H Functionalization of Carbamoyl-Protected Indoles Using Alkynes2.4 C–H Allylation Using Allyl Alcohols2.5 Cyclization Reactions of O-Acyloximes and Alkynes2.6 Other Miscellaneous Reactions3 Enantioselective C–H Functionalization Reactions by Hybrid Catalysis3.1 Cp*RhIII/Chiral Disulfonate Catalysts for the Enantioselective C–H Addition to Enones3.2 Enantioselective C–H Cleavage Using Chiral Carboxylic Acids4 Summary and Perspective

scholarly journals Anodic coupling of carboxylic acids to electron-rich double bonds: A surprising non-Kolbe pathway to lactones

2013 ◽  
Vol 9 ◽  
pp. 1630-1636 ◽  
Author(s):  
Robert J Perkins ◽  
Hai-Chao Xu ◽  
John M Campbell ◽  
Kevin D Moeller
Keyword(s):  
Carboxylic Acids ◽  
Radical Cation ◽  
Experimental Results ◽  
Double Bonds ◽  
Reaction Proceeds

Carboxylic acids have been electro-oxidatively coupled to electron-rich olefins to form lactones. Kolbe decarboxylation does not appear to be a significant competing pathway. Experimental results indicate that oxidation occurs at the olefin and that the reaction proceeds through a radical cation intermediate.

Utility of the Cleavage of Nitrosamides for the Preparation of Chiral Acids after Chromatographic Separation of their Diastereomeric Amides

1977 ◽  
Vol 32 (1) ◽  
pp. 98-104 ◽  
Author(s):  
Franz P. Schmidtchen ◽  
Peter Rauschenbach ◽  
Helmut Simon
Keyword(s):  
Double Bond ◽  
Carboxylic Acids ◽  
Chromatographic Separation ◽  
Optical Resolution ◽  
Double Bonds ◽  
Reaction Conditions ◽  
Double Bond Migration ◽  
Enantiomerically Pure ◽  
Amide Derivatives ◽  
Derivatives Of

A method for optical resolution of chiral acids is described. It consists of the conversion of racemic acids to diastereomeric amides, their chromatographic separation and subsequent deamidation via the nitrosamide route. Reaction conditions for cleavage of amide derivatives of phenylalanine and methylbenzylamine are given. No or only negligible racemization of carboxylic acids, chiral in α-position takes place under those conditions. The extent of Ε,Ζ-isomerization of double bonds is very small, as is the extent of double bond migration from the Δ3-position into conjugation with the carboxyl function. Enantiomerically pure R- or S[2-3H]2-methylbutanoic acid and (-)methyl-3(p-chlorophenyl)-2-chloropropionate (Bidisin®) were prepared by this procedure.

Sign in / Sign up

Export Citation Format

Share Document