Remodelling of Tricyclic Carbon Frameworks with a Norbornene Scaffold

Akihiro Yoshitani; Tomonari Sasage; Ranmaru Kato; Takahiro Suzuki; Kazutada Ikeuchi; Keiji Tanino

doi:10.1039/d5cc04790k

January 1, 2025Chemical Communications

Remodelling of Tricyclic Carbon Frameworks with a Norbornene Scaffold

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Key Points

The rearrangement yields a structurally new tricyclic compound, enhancing synthetic pathways for complex frameworks.
Skeletal rearrangement led to the formation of a tricyclo[4.2.1.03,7]nonane skeleton from tricyclo[4.3.0.03,7]non-8-ene derivatives.
The process utilizes specific hydroxy and silyloxy substitutions, indicating the importance of these groups in the reaction.
The findings provide insights into potential applications for creating novel organic materials and structures.

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Implication

This research demonstrates a halogen-mediated skeletal rearrangement of tricyclic compounds, yielding a new carbon scaffold.

Abstract

We describe a halogen/chalcogen-mediated skeletal rearrangemnt of tricyclo[4.3.0.03,7]non-8-ene derivatives that feature a norbornene framework with two hydroxy/silyloxy groups substituted on the bridgehead carbons, yielding a tricyclo[4.2.1.03,7]nonane (brendane) skeleton. Four different...

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Yoshitani et al. (2025) studied this question.

synapsesocial.com/papers/68c18f469b7b07f3a0616344 https://doi.org/10.1039/d5cc04790k

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Remodelling of Tricyclic Carbon Frameworks with a Norbornene Scaffold

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Remodelling of Tricyclic Carbon Frameworks with a Norbornene Scaffold

Key Points

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Abstract

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