Synthesis of 5,6-Disubstituted Bicyclo[2.1.1]Hexanes as Potential Rigidified 1,3-Disubstituted Cyclobutanes

Strategies for the synthesis of 5,6-disubstituted bicyclo[2.1.1]hexanes are presented. These target molecules are of high value because we propose that they might act as rigidified variants of 1,3-disubstituted cyclobutanes. Key to the strategy is the use of a photochemical Wolff rearrangement. Several diastereoselective transformations are provided to showcase their utility.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-07-17
DOI
https://doi.org/10.1021/acs.joc.6c00975
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis of 5,6-Disubstituted Bicyclo[2.1.1]Hexanes as Potential Rigidified 1,3-Disubstituted Cyclobutanes

M. Kevin Brown, Shashwati Paul
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Synthesis of 5,6-Disubstituted Bicyclo[2.1.1]Hexanes as Potential Rigidified 1,3-Disubstituted Cyclobutanes

M. Kevin Brown, Shashwati Paul
article en

Abstract

Strategies for the synthesis of 5,6-disubstituted bicyclo[2.1.1]hexanes are presented. These target molecules are of high value because we propose that they might act as rigidified variants of 1,3-disubstituted cyclobutanes. Key to the strategy is the use of a photochemical Wolff rearrangement. Several diastereoselective transformations are provided to showcase their utility.

The Journal of Organic Chemistry
Indiana University Bloomington (US)
Foundation for the National Institutes of Health, Indiana University
Openalex Percentile: Top 15%
Radical Photochemical Reactions
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