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Tropylium Ion Mediated α-cyanation of Amines

Julia M Allen, Tristan H Lambert

J Am Chem Soc. 2011 Feb 9;133(5):1260-2.

PMID: 21204541

Abstract:

Tropylium ion mediated α-cyanation of amines is described. Even in the presence of KCN, tropylium ion is capable of oxidizing various amine substrates, and the resulting iminium ions undergo salt metathesis with cyanide ion to produce aminonitriles. The byproducts of this transformation are simply cycloheptatriene, a volatile hydrocarbon, and water-soluble potassium tetrafluoroborate. Thirteen total substrates are shown for the α-cyanation procedure, including a gram scale synthesis of 17β-cyanosparteine. In addition, a tropylium ion mediated oxidative aza-Cope rearrangement is demonstrated.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP14075537 Potassium tetrafluoroborate Potassium tetrafluoroborate 14075-53-7 Price
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