Synthesis of Substituted Iptycenes

Ying-Xian Ma; Zheng Meng; Chuan-Feng Chen

doi:10.1055/s-0034-1379361

Synlett, Table of Contents

Synlett 2015; 26(01): 6-30
DOI: 10.1055/s-0034-1379361

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Synthesis of Substituted Iptycenes

Ying-Xian Ma

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +86(10)62554449 Email: cchen@iccas.ac.cn

,

Zheng Meng

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +86(10)62554449 Email: cchen@iccas.ac.cn

,

Chuan-Feng Chen*

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +86(10)62554449 Email: cchen@iccas.ac.cn

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Abstract

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Abstract

Iptycenes are a class of aromatic compounds that contain several arene units fused to a bicyclo[2.2.2]octatriene bridgehead system. This unique, rigid, three-dimensional molecular structure provides several open electron-rich cavities with an abundance of reactive positions, and makes them useful for a wide range of applications. There is no doubt that the synthesis and reactions of iptycene derivatives with different functional groups form the fundamental basis of iptycene development. In this account, the synthesis of substituted iptycenes is described. In particular, the different synthetic strategies toward substituted triptycenes and pentiptycenes are the main focus.

1 Introduction

2 Synthesis of Substituted Triptycenes

2.1 Direct Diels–Alder Addition Reactions

2.2 Selective Substitution of the Triptycene Skeleton

2.2.1 Acetylation

2.2.2 Nitration

2.2.3 Halogenation

3 Synthesis of Substituted Pentiptycenes

4 Synthesis of Other Substituted Iptycenes

5 Conclusion and Outlook

Key words

acylation - Diels–Alder reaction - electrophilic addition - halogenation - substituent effects

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References

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