TCI C1266 Ethyl Cyanoformate (CAS 623-49-4), widely known as Mander's reagent, is a highly reactive electrophilic reagent for carbon-selective acylation. It reacts with lithium enolates to give beta-keto esters with strong preference for C-acylation over O-acylation, which is why it appears at key steps in terpenoid, steroid, and alkaloid total syntheses. The reagent also converts amines into ethyl carbamates and participates in selected cycloaddition chemistry. AMI Scientific supplies 5 g and 25 g packs; because the material is toxic and moisture-sensitive, it must be handled in a fume hood under dry conditions with careful review of the TCI Safety Data Sheet.
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- North et al. (2014). Kinetics and mechanism of base catalysed ethyl cyanoformate addition to aldehydes. Tetrahedron doi:10.1016/j.tet.2014.02.009
- GILCHRIST et al. (1993). ChemInform Abstract: Reaction of Pyrroles with Ethyl 2‐Nitroso‐ and 2‐Azo‐propenoates, and with Ethyl Cyanoformate N‐Oxide: A Comparison of the Reaction Pathways.. ChemInform doi:10.1002/chin.199345109
- Aoki et al. (2010). DMAP-catalyzed cyanation of aldehydes and ketones with ethyl cyanoformate. Tetrahedron Letters doi:10.1016/j.tetlet.2010.04.123
References were compiled automatically from Crossref and every DOI was verified to exist. AMI Scientific is not affiliated with the authors or the publishers.
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