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Synlett 2015; 26(01): 6-30
DOI: 10.1055/s-0034-1379361
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© Georg Thieme Verlag Stuttgart · New York

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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Further Information

Publication History

Received: 30 August 2014

Accepted after revision: 26 September 2014

Publication Date:
02 December 2014 (online)

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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