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

Research output: Contribution to journalArticle

6 Citations (Scopus)

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 diaryl ethene 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.

Original languageEnglish
Pages (from-to)2949-2957
Number of pages9
JournalSynthesis (Germany)
Volume49
Issue number13
DOIs
Publication statusPublished - Jul 3 2017

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Keywords

  • flow reaction
  • Mallory photocyclization
  • phenacene
  • photochemistry
  • Wittig reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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