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Synlett 2017; 28(09): 1018-1027
DOI: 10.1055/s-0036-1588153
DOI: 10.1055/s-0036-1588153
account
Thieme Chemistry Journals Awardees – Where Are They Now? Aromaticity as a Source for Strain Energy? Synthesis of Curved Polycyclic Aromatic Structures via [2+2+2] Cycloaddition Reactions
Further Information
Publication History
Received: 11 January 2017
Accepted after revision: 15 February 2017
Publication Date:
08 March 2017 (online)
Abstract
This account describes synthetic approaches for curved polycyclic aromatics such as circulenes, helicenes and cycloparaphenylenes, relying on a [2+2+2] cycloaddition. A common feature of all these structures is that their synthesis needs to deviate benzene rings from planarity. Relying on [2+2+2] cycloaddition reactions for this task leads to impressive, and in parts, surprising results. The examples shown here and their optimized reaction conditions contribute to a better understanding of processes going on during the reaction. This knowledge is expected to lead to new designs of challenging syntheses using the [2+2+2] cycloaddition methodology.
1 No Gain, No Strain: Synthesis of Curved Aromatics
2 Examples for the Preparation of Strained Systems Relying on a [2+2+2] Cycloaddition
2.1 Circulenes
2.2 Helicenes
2.3 Cycloparaphenylenes
3 Conclusion and Outlook
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