Abstract
This article describes the discovery and recent progresses of cyclobutanonebased free radical ring expansion and annulation reactions. Mechanisms associated with these reaction processes are also discussed. Ring expansion reactions rely on selective β- scission of alkoxy radicals generated from the cyclization of carbon radicals onto carbonyls. Exo-substituted cyclobutanones are employed to construct cis-fused seven- and eight-membered rings, spiro-annulated medium rings, large rings, and cyclopropanecontaining compounds. Endo-substituted cyclobutanones can undergo tandem rearrangements to produce bridged rings. The cyclization of dichlorocyclobutanones followed by TMSI-induced ring opening is another ring expansion strategy for the construction of some novel ring systems. Cyclobutanones used for free radical reactions are readily prepared by well-established [2 + 2] cycloadditions of ketenes with various olefins.
Keywords: Cyclobutanone, Free Radical Ring, FUSED-KETONES, BENZOSUBERONES
Current Organic Chemistry
Title: Discovery and Development of Cyclobutanone-Based Free Radical Ring Expansion and Annulation Reactions
Volume: 6 Issue: 11
Author(s): Wei Zhang
Affiliation:
Keywords: Cyclobutanone, Free Radical Ring, FUSED-KETONES, BENZOSUBERONES
Abstract: This article describes the discovery and recent progresses of cyclobutanonebased free radical ring expansion and annulation reactions. Mechanisms associated with these reaction processes are also discussed. Ring expansion reactions rely on selective β- scission of alkoxy radicals generated from the cyclization of carbon radicals onto carbonyls. Exo-substituted cyclobutanones are employed to construct cis-fused seven- and eight-membered rings, spiro-annulated medium rings, large rings, and cyclopropanecontaining compounds. Endo-substituted cyclobutanones can undergo tandem rearrangements to produce bridged rings. The cyclization of dichlorocyclobutanones followed by TMSI-induced ring opening is another ring expansion strategy for the construction of some novel ring systems. Cyclobutanones used for free radical reactions are readily prepared by well-established [2 + 2] cycloadditions of ketenes with various olefins.
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Cite this article as:
Zhang Wei, Discovery and Development of Cyclobutanone-Based Free Radical Ring Expansion and Annulation Reactions, Current Organic Chemistry 2002; 6 (11) . https://dx.doi.org/10.2174/1385272023373707
DOI https://dx.doi.org/10.2174/1385272023373707 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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