Convenient Phenacene Synthesis by Sequentially Performed Wittig­ Reaction and Mallory Photocyclization Using Continuous-Flow Techniques

Hideki Okamoto; Haruhiko Takahashi; Takamitsu Takane; Yasuhiro Nishiyama; Kiyomi Kakiuchi; Shin Gohda; Minoru Yamaji

doi:10.1055/s-0036-1588775

Synthesis, Table of Contents

Synthesis 2017; 49(13): 2949-2957
DOI: 10.1055/s-0036-1588775

paper

Convenient Phenacene Synthesis by Sequentially Performed Wittig Reaction and Mallory Photocyclization Using Continuous-Flow Techniques

Authors

Hideki Okamoto*

^aDivision of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University, Tsushima-Naka 3-1-1, Okayama 700-8350, Japan
Haruhiko Takahashi

^aDivision of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University, Tsushima-Naka 3-1-1, Okayama 700-8350, Japan
Takamitsu Takane

^aDivision of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University, Tsushima-Naka 3-1-1, Okayama 700-8350, Japan
Yasuhiro Nishiyama

^bGraduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama, Ikoma, Nara 630-0192, Japan
Kiyomi Kakiuchi

^bGraduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama, Ikoma, Nara 630-0192, Japan
Shin Gohda

^cMaterial Science Research Group, NARD Institute, Ltd., Nishinagasu-cho 2-6-1, Amagasaki, Hyogo 660-0805, Japan
Minoru Yamaji

^dDivision of Molecular Science, Graduate School of Science and Engineering, Gunma University, Kiryu, Gunma 376-8515, Japan Email: hokamoto@okayama-u.ac.jp

Abstract

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Abstract

Various phenacenes possessing chrysene, picene, and fulminene frameworks were prepared by using a continuous-flow synthetic protocol in which Wittig reaction affording diarylethenes and their Mallory photocyclization producing phenacene skeletons were sequentially performed. The Wittig reaction solution, containing the diarylethene obtained from an arylaldehyde and an arylmethyltriphenylphosphonium salt, was mixed with an iodine solution in the flow system and, subsequently, the solution was subjected to the photoreaction. Desired phenacenes were obtained with high to moderate chemical yield. For the present protocol, isolation of the intermediary diarylethene, which is the key precursor of the phenacene, is unnecessary. The approach provides a convenient method to supply a variety of phenacene samples, which are needed for initial systematic surveys in material science.

Key words

phenacene - flow reaction - Mallory photocyclization - Wittig reaction - photochemistry

Full Text

References

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Convenient Phenacene Synthesis by Sequentially Performed Wittig­ Reaction and Mallory Photocyclization Using Continuous-Flow Techniques

Authors

Convenient Phenacene Synthesis by Sequentially Performed Wittig Reaction and Mallory Photocyclization Using Continuous-Flow Techniques