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Exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane.

ABSTRACT: Bicyclo[1.1.1]pentane (BCP) has received substantial interest in the field of synthetic chemistry recently for its potential use as a benzene isostere in medicinal chemistry. Whereas bicyclo[2.2.2]octane (BCO) has also been used as a bioisostere of benzene, the condensation of BCP-amine with nadic anhydride is significantly easier than that of BCO-amine. Analyses of the geometries and the frontier molecular orbitals of these amines suggest that the low steric hindrance and high intrinsic nucleophilicity of BCP-amine together contribute to its exceptional reactivity.

SUBMITTER: Lu Y

PROVIDER: S-EPMC10544781 | biostudies-literature | 2023

REPOSITORIES: biostudies-literature

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Exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane.

Lu Yong Y Chen Chuo C

ARKIVOC : free online journal of organic chemistry 20230823 Pt 2

Bicyclo[1.1.1]pentane (BCP) has received substantial interest in the field of synthetic chemistry recently for its potential use as a benzene isostere in medicinal chemistry. Whereas bicyclo[2.2.2]octane (BCO) has also been used as a bioisostere of benzene, the condensation of BCP-amine with nadic anhydride is significantly easier than that of BCO-amine. Analyses of the geometries and the frontier molecular orbitals of these amines suggest that the low steric hindrance and high intrinsic nucleop ...[more]

PMID: 37786812

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Light-enabled scalable synthesis of bicyclo[1.1.1]pentane halides and their functionalizations.

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