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

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 rea...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2017-07, Vol.49 (13), p.2949-2957
Main Authors: Okamoto, Hideki, Takahashi, Haruhiko, Takane, Takamitsu, Nishiyama, Yasuhiro, Kakiuchi, Kiyomi, Gohda, Shin, Yamaji, Minoru
Format: Article
Language:English
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1588775