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.
![Synthesis of Bicyclo[1.1.1]pentane Carboxamides and Ketones from [1.1.1]Propellane](/_next/image?url=%2F_next%2Fstatic%2Fmedia%2Fplaceholder.5ca6fc18.png&w=256&q=75)
![Synthesis of Bicyclo[1.1.1]pentane Carboxamides and Ketones from [1.1.1]Propellane](/_next/image?url=https%3A%2F%2Fcdn.gdch.de%2Fprod%2Fnadc20264158444_fig_0001_a_36fd5c002c.png&w=256&q=75)
![Synthesis of Bicyclo[1.1.1]pentane Carboxamides and Ketones from [1.1.1]Propellane](/_next/image?url=https%3A%2F%2Fcdn.gdch.de%2Fprod%2Fnadc20264158499_fig_0001_a_8463b1bf14.png&w=256&q=75)
![Synthesis of Bicyclo[1.1.1]pentane Carboxamides and Ketones from [1.1.1]Propellane](/_next/image?url=https%3A%2F%2Fcdn.gdch.de%2Fprod%2Fnadc20264158504_gra_0001_a_6653df00f8.png&w=256&q=75)
