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Borole/Borapyramidane Relationship.

Qiu Sun¹, Constantin G Daniliuc¹, Xiaoye Yu¹

¹Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.

Journal of the American Chemical Society

|April 19, 2022

Summary

This summary is machine-generated.

Boroles and borapyramidanes are constitutional isomers that can be interconverted. This study demonstrates their rearrangement via hydroboration, photolysis, and thermolysis, revealing new structural insights.

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Area of Science:

Organoboron Chemistry
Isomerism in Organic Molecules
Synthetic Chemistry

Background:

Boroles and borapyramidanes represent classical and nonclassical constitutional isomers.
Understanding their interconversion is crucial for exploring novel molecular architectures.
Previous studies have not extensively detailed the direct conversion pathways between these isomers.

Purpose of the Study:

To demonstrate the interconversion between boroles and borapyramidanes.
To investigate the synthetic routes and reaction conditions for these transformations.
To characterize the resulting isomers and understand their structural properties.

Main Methods:

Synthesis of a bis(alkynyl)B(C6F5) SMe2 adduct.
1,1-hydroboration/alkenylboration sequence.
Photolysis and thermolysis of borole and borapyramidane intermediates.
Characterization using X-ray diffraction and DFT calculations.

Main Results:

Successful interconversion between borole 1·SMe2 and borapyramidane 2 was achieved.
Photolysis of borole 1·SMe2 yielded borapyramidane 2 in high yield.
Thermolysis and photolysis experiments revealed pathways to other borapyramidane isomers (10).

Conclusions:

Boroles and borapyramidanes can be reversibly interconverted under specific reaction conditions.
This work expands the known chemistry of these organoboron compounds.
The study provides valuable insights into the structural dynamics and reactivity of borole and borapyramidane systems.