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Synthesis of Bicyclo[1.1.0]butanes from Bicyclo[1.1.1]pentanes

02 May 2023, Version 1

Abstract

We describe a two step process for the synthesis of substituted bicyclo[1.1.0]butanes. A photo-Hunsdiecker reaction generates iodo-bicyclo[1.1.1]pentanes under metal-free conditions at room temperature. These intermediates react with amine and thiol nucleophiles to afford substituted bicyclo[1.1.0]butane products.

Keywords

Bicyclo[1.1.1]pentanes
BCP
Bicyclo[1.1.0]butanes
BCB
Phenyl bioisosteres
Photo-Hunsdiecker
Skeletal Editing

Supplementary materials

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Description
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Title
Electronic Supplementary Information
Description
General procedures, NMR data, X-ray crystallographic data.
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Version History

May 02, 2023 Version 1

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The content is available under CC BY 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2023-z8jvt
D O I: 10.26434/chemrxiv-2023-z8jvt [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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