Synthesis of Bicyclo[1.1.1]pentane Carboxamides and Ketones from [1.1.1]Propellane

A convenient method for acylation of [1.1.1]propellane to give bicyclo[1.1.1]pentane (BCP) carboxamides and ketones has been developed. It provides a straightforward one-step access to monosubstituted BCP carboxamides, synthesis of which requires multiple chemical steps in previous reports.

Abstract

Bicyclo[1.1.1]pentane (BCP) carboxamides are prepared from the direct addition of [1.1.1]propellane with semicarbazides in the presence of iron(II) phthalocyanine {Fe(Pc)} and tert-butyl hydroperoxide (TBHP) in moderate to good yields. BCP ketones are also obtained under similar conditions in moderate yields. This protocol provides a straightforward one-step access to BCP carboxamides, synthesis of which requires multiple chemical steps in previous reports.

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