ChemInform Abstract: Enabling the Synthesis of Perfluoroalkyl Bicyclobutanes via 1,3 γ‐Silyl Elimination.

Kelly, Carmel; Colthart, Allison M.; Constant, Brad D.; Corning, S.; Dubois, Lily; Genovese, Jacqueline; Radziewicz, Julie L.; Sletten, Ellen M.; Whitaker, Katherine R.; Tilley, Leon J.

doi:10.1002/chin.201125051

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Synthesis Of Bicyclobutanes1

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2023

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“…This approach can provide access to different bridgehead disubstituted BCBs, but the incorporation of the second substituent in the first step and three subsequent transformations makes it a relatively time-consuming approach. Tilley and coworkers reported a related transannular cyclisation approach, using an unusual 1,3 γ-silyl elimination to form the BCB (not shown) 40 .…”

Section: Synthesis Of Bicyclobutanesmentioning

confidence: 99%

Bicyclobutanes as unusual building blocks for complexity generation in organic synthesis

Golfmann

Walker

2023

Commun Chem

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Bicyclobutanes are among the most highly strained isolable organic compounds and their associated low activation barriers to reactivity make them intriguing building-blocks in organic chemistry. In recent years, numerous creative synthetic strategies exploiting their heightened reactivity have been presented and these discoveries have often gone hand-in-hand with the development of more practical routes for their synthesis. Their proclivity as strain-release reagents through their weak central C–C bond has been harnessed in a variety of addition, rearrangement and insertion reactions, providing rapid access to a rich tapestry of complex molecular scaffolds. This review will provide an overview of the different options available for bicyclobutane synthesis, the main classes of compounds that can be prepared from bicyclobutanes, and the associated modes of reactivity used.

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Section: Synthesis Of Bicyclobutanesmentioning

confidence: 99%