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20.2.1.1 Synthesis from Carbonic Acid Derivatives

DOI: 10.1055/sos-SD-020-00036

Collier, S. J.; Kataisto, E.Science of Synthesis, (20072053.

General Introduction

This contribution reviews the synthesis of alkanoic acids from carbonic acid derivatives. Previously published information on this subject can be found in HoubenWeyl, Vol. E5, pp 323361 and 470482 and in several other reviews.[‌1‌‌4‌] The syntheses of aryl, alk-2-enyl, alk-2-ynyl, and 2- and 3-heteroatom-substituted carboxylic acids are not discussed in any detail, but are covered elsewhere in this volume. Much of the chemistry covered in this section involves the reactions of carbon dioxide (Section 20.2.1.1.1). A second important, but less widely used, class of reactions involving carbonic acid derivatives utilizes methyl methoxymagnesium carbonate (MMC, Stiles' reagent). Since the products of such reactions are primarily β-oxo acids, this chemistry is discussed in more detail in Section 20.2.12. However, carboxylations of nitroalkanes with methyl methoxymagnesium carbonate, and some carboxylations with related reagents, are mentioned in Section 20.2.1.1.2. In the interests of simplicity, both carboxylic acids and their salts will be considered together and differentiation will only be made when there is a significant reason, such as a notable change in stability between the two species.

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