Facile Synthesis of Cyclic Polyphenylenes by Consecutive Inter- and Intramolecular Cycloadditions of ortho-, meta-, and para-Phenylene-Tethered Triynes

Takanori Shibata; Masako Fujimoto; Hiroyuki Hirashima; Tatsuya Chiba; Kohei Endo

doi:10.1055/s-0032-1316793

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(21): 3269-3284
DOI: 10.1055/s-0032-1316793

feature article

Facile Synthesis of Cyclic Polyphenylenes by Consecutive Inter- and Intramolecular Cycloadditions of ortho-, meta-, and para-Phenylene-Tethered Triynes

Takanori Shibata*

^aDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan

,

Masako Fujimoto

^aDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan

,

Hiroyuki Hirashima

^aDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan

,

Tatsuya Chiba

^aDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan

,

Kohei Endo

^bSchool of Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan Fax: +81(3)52868098 eMail: tshibata@waseda.jp

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Abstract

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Abstract

Consecutive inter- and intramolecular [2+2+2] cycloadditions of various phenylene-tethered triynes were comprehensively studied by using chiral rhodium catalysts. ortho-Phenylene-tethered triynes gave chiral o,o,o,o-tetraphenylenes in high-to-excellent enantiomeric excess as dimers. meta-Phenylene-tethered triynes gave chiral o,m,o,m-tetraphenylenes in moderate enantiomeric excess as dimers along with hexaphenylenes as trimers. This is the first synthesis of cis-o,m,o,m-tetraphenylenes; one structure was ascertained by X-ray crystal structure analysis. para-Phenylene-tethered triynes gave o,p,o,p,o,p-hexaphenylenes as trimers along with the formation of o,p,o,p,o,p,o,p-octaphenylenes as tetramers.

1 Introduction

2 Results and Discussion

2.1 ortho-Phenylene-Tethered Triynes

2.2 Naphthylene-Tethered Triynes

2.3 meta-Phenylene-Tethered Triynes

2.4 para-Phenylene-Tethered Triynes

3 Conclusion

Key words

polyphenylenes - axial chirality - cycloaddition - asymmetric synthesis - chiral catalysts - rhodium

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Referenzen

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