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20.5.1.1.1 Method 1: Use of Carbonic Acid Diesters

DOI: 10.1055/sos-SD-020-00643

Collier, S. J.Science of Synthesis, (200720665.

Carbonic acid diesters, particularly dialkyl carbonates, have been used to prepare carboxylic acid esters for many years. Generally, the carbonates participate in intermolecular condensations with carbon nucleophiles, but intramolecular rearrangements resulting in carboxylic acid ester formation have also been reported. In the case of dimethyl and dibenzyl carbonate, it should be noted that a competing alkylation reaction can occur at high temperatures (>120°C), although this does not usually present a problem.[‌8‌] The following sections are categorized by the nature of the nucleophilic carbon fragment involved in the acylation reaction. Most commonly, enolates (derived from ketones or esters) and organometallic carbanions (with and without α-heteroatom stabilization) are used in these reactions. Intramolecular rearrangements of carbonates which yield alkanoyl esters are discussed in the final section.

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