Synlett 2016; 27(12): 1765-1774
DOI: 10.1055/s-0035-1561617
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© Georg Thieme Verlag Stuttgart · New York

Aromatic Metamorphosis of Dibenzothiophenes

Hideki Yorimitsu*
a  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan
b  Institute for Molecular Science, Okazaki, Aichi 444-8787, Japan
,
Dhananjayan Vasu
a  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan
,
M. Bhanuchandra
a  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan
,
Kei Murakami
a  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan
c  The Hakubi Center for Advanced Research, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan   Email: [email protected]
,
Atsuhiro Osuka
a  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan
› Author Affiliations
Further Information

Publication History

Received: 12 February 2016

Accepted: 11 March 2016

Publication Date:
18 May 2016 (online)


Abstract

In general, aromatic cores are stable owing to their resonance energies. Different from facile peripheral modifications of aromatic cores, transforming an aromatic core into a different skeleton is ambitious and has attracted only little attention as a general synthetic method. This personal account shows our journey to inventing transformations of dibenzothiophenes into triphenylenes, carbazoles, and spirocyclic diarylfluorenes and to establishing ‘aromatic metamorphosis’ as a useful and game-changing strategy in organic synthesis.

1 Introduction

2 Aromatic Metamorphosis

3 From Dibenzothiophenes to Triphenylenes

4 From Dibenzothiophenes to Carbazoles

5 From Dibenzothiophenes to Spirocyclic Tetraarylmethanes

6 Conclusion

 
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  • 2 Current address: Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan.
  • 3 Current address: Department of Chemistry, School of Chemical Sciences and Pharmacy, Central University of Rajasthan, Bandarsindri, Rajasthan 305817, India.
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