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20.5.1.1.3 Method 3: Use of Cyanoformate Esters

DOI: 10.1055/sos-SD-020-00643

Collier, S. J.Science of Synthesis, (200720693.

Although they are not truly carbonic acid derivatives, cyanoformate esters are included in this section because they exhibit similar chemistry. However, whereas cyanoformates are milder acylating agents than chloroformates, they are more reactive than carbonate di­esters. This selective activity has its uses, but the value of cyanoformates in synthesis is tempered by the release of highly toxic cyanide ion as a byproduct. Moreover, metal cyanides are also somewhat nucleophilic, so care must also be taken with substrates bearing reactive electrophilic centers (see below). A range of alkyl cyanoformates have been reported, but methyl cyanoformate, sometimes known as Mander's reagent,[‌196‌] is the most commonly encountered.

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